- Propargylation of CoQ0 through the Redox Chain Reaction
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An efficient catalytic propargylation of CoQ0 is described by employing the cooperative effect of Sc(OTf)3 and Hantzsch ester. It is suggested to work through the redox chain reaction, which involves hydroquinone and dimeric propargylic moiety intermediates. A broad range of propargylic alcohols can be converted into the appropriate derivatives of CoQ0 containing triple bonds in good to excellent yields. The mechanism of the given transformation is also discussed.
- Mlynarski, Jacek,Pawlowski, Robert,Stodulski, MacIej
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- Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition
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A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed. (Figure presented.).
- Pradhan, Tapas R.,Mohapatra, Debendra K.
-
supporting information
p. 3605 - 3611
(2019/07/04)
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- Trialkylborane-Mediated Propargylation of Aldehydes Using γ-Stannylated Propargyl Acetates
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A transition-metal-free three-component process that combines aldehydes, 3-(tributylstannyl)propargyl acetates formed in situ from readily available propargyl acetates, and trialkylboranes provides access to a range of 1,2,4-trisubstituted homopropargylic alcohols. The addition of diisopropylamine plays a crucial role in the selective formation of homopropargylic alcohols. Importantly, this methodology can be extended to a single-flask reaction sequence starting from propargyl acetates.
- Horino, Yoshikazu,Murakami, Miki,Ishibashi, Mayo,Lee, Jun Hee,Watanabe, Airi,Matsumoto, Rio,Abe, Hitoshi
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supporting information
p. 9564 - 9568
(2019/12/24)
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- Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols
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The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.
- Horino, Yoshikazu,Murakami, Miki,Aimono, Ataru,Lee, Jun Hee,Abe, Hitoshi
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supporting information
p. 476 - 480
(2019/01/14)
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- Palladium- and Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles
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A complementing Pd- and Rh-catalyzed dynamic kinetic resolution (DKR) of racemic allenes leading to N-allylated pyrazoles is described. Such compounds are of enormous interest in medicinal chemistry as certified drugs and potential drug candidates. The new methods feature high chemo-, regio- and enantioselectivities aside from displaying a broad substrate scope and functional group compatibility. A mechanistic rational accounting for allene racemization and trans-alkene selectivity is discussed.
- Hilpert, Lukas J.,Sieger, Simon V.,Haydl, Alexander M.,Breit, Bernhard
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supporting information
p. 3378 - 3381
(2019/02/06)
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- One-pot synthesis of polyfunctionalized quinolines: Via a copper-catalyzed tandem cyclization
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An efficient one-pot approach for the synthesis of polyfunctionalized quinolines was developed via a sequence of copper-catalyzed coupling reaction/propargyl-allenyl isomerization/aza-electrocyclization. Easily available starting materials, mild conditions, and a wide substrate scope make this approach potentially useful.
- Chen, Dianpeng,Sun, Xuejun,Shan, Yingying,You, Jinmao
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supporting information
p. 7657 - 7662
(2018/11/02)
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- Metal- and Acid-Free Methyl Triflate Catalyzed Meyer-Schuster Rearrangement
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A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer-Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and E -enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.
- Yang, Lu,Zeng, Qingle
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p. 3149 - 3156
(2017/07/12)
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- Palladium-Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7-Membered Carbocycles
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Palladium(II) acetate in association with secondary phosphine oxides provides an efficient catalytic system for [2+1] cycloadditions starting from oxanorbornene derivatives and tertiary propargyl esters giving rise to vinylidenecyclopropanes. This reaction is specific to bidentate phosphinito-phosphinous acid ligands generated from secondary phosphine oxides. The [2+1] cycloaddition was found broad in scope with a high tolerance to various functional groups. Moreover, vinylidenecyclopropanes were straightforwardly converted into oxabicyclo[3.2.1]oct-2-ene derivatives through a palladium-catalyzed ring-expansion. Finally, the oxa bridge cleavage of oxatricyclic compounds yields functionalized 7-membered carbocycles.
- Lepronier, Aymeric,Achard, Thierry,Giordano, Laurent,Tenaglia, Alphonse,Buono, Gerard,Clavier, Herve
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supporting information
p. 631 - 642
(2016/02/27)
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- Cu-Pybox catalyzed synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and propargyl alcohol derivatives
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A highly efficient cascade sequence for syntheses of 2,3-disubstituted imidazo[1,2-a]pyridines with exclusive regioselectivity in moderate to excellent yields has been developed. This cascade was initiated through propargylation of 2-aminopyridines at pyridine-nitrogen with propargyl alcohol derivatives using Cu(II)-Pybox as catalyst and followed by an intramolecular cyclization and isomerization. Besides 2-aminopyridine, less reactive 2-aminopyrimidine, 2-aminopyrazine and 3-aminopyridazine were also suitable in this cascade.
- Cheng, Cang,Ge, Luo,Lu, Xuehe,Huang, Jianping,Huang, Haocheng,Chen, Jie,Cao, Weiguo,Wu, Xiaoyu
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p. 6866 - 6874
(2016/10/04)
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- Diversification of ortho-Fused Cycloocta-2,5-dien-1-one Cores and Eight- to Six-Ring Conversion by σ Bond C?C Cleavage
-
Sequential treatment of 2-C6H4Br(CHO) with LiC≡CR1(R1=SiMe3, tBu), nBuLi, CuBr?SMe2and HC≡CCHClR2[R2=Ph, 4-CF3Ph, 3-CNPh, 4-(MeO2C)Ph] at ?50 °C leads to formation of an intermediate carbanion (Z)-1,2-C6H4{CA(=O)C≡CBR1}{CH=CH(CH?)R2} (4). Low temperatures (?50 °C) favour attack at CBleading to kinetic formation of 6,8-bicycles containing non-classical C-carbanion enolates (5). Higher temperatures (?10 °C to ambient) and electron-deficient R2favour retro σ-bond C?C cleavage regenerating 4, which subsequently closes on CAproviding 6,6-bicyclic alkoxides (6). Computational modelling (CBS-QB3) indicated that both pathways are viable and of similar energies. Reaction of 6 with H+gave 1,2-dihydronaphthalen-1-ols, or under dehydrating conditions, 2-aryl-1-alkynylnaphthlenes. Enolates 5 react in situ with: H2O, D2O, I2, allylbromide, S2Me2, CO2and lead to the expected C-E derivatives (E=H, D, I, allyl, SMe, CO2H) in 49–64 % yield directly from intermediate 5. The parents (E=H; R1=SiMe3, tBu; R2=Ph) are versatile starting materials for NaBH4and Grignard C=O additions, desilylation (when R1=SiMe) and oxime formation. The latter allows formation of 6,9-bicyclics via Beckmann rearrangement. The 6,8-ring iodides are suitable Suzuki precursors for Pd-catalysed C?C coupling (81–87 %), whereas the carboxylic acids readily form amides under T3P conditions (71–95 %).
- Eccleshare, Lee,Lozada-Rodríguez, Leticia,Cooper, Phillippa,Burroughs, Laurence,Ritchie, John,Lewis, William,Woodward, Simon
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supporting information
p. 12542 - 12547
(2016/08/24)
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- Convenient synthesis of allenylphosphoryl compounds: Via Cu-catalysed couplings of P(O)H compounds with propargyl acetates
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A novel Cu-catalysed substitution reaction of propargyl acetates with P(O)H compounds is developed to afford allenylphosphoryl compounds via C-P bond coupling in high yields under mild conditions. A plausible mechanism involving the nucleophilic interception of the Cu-allenylidene intermediates is proposed.
- Shen, Ruwei,Luo, Bing,Yang, Jianlin,Zhang, Lixiong,Han, Li-Biao
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supporting information
p. 6451 - 6454
(2016/05/24)
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- Synthesis of 1,2,3-Substituted Pyrroles from Propargylamines via a One-Pot Tandem Enyne Cross Metathesis-Cyclization Reaction
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Enyne cross metathesis of propargylamines with ethyl vinyl ether enables the one-pot synthesis of substituted pyrroles. A series of substituted pyrroles, bearing alkyl, aryl, and heteroaryl substituents, has been synthesized in good yields under microwave irradiation. The reactions are rapid and procedurally simple and also represent a facile entry to the synthetically challenging 1,2,3-substituted pyrroles. The value of the methodology is further corroborated by the conversion of pyrroles into 3-methyl-pyrrolines and the derivatization of the 3-methyl-substituent arising from the metathesis reaction.
- Chachignon, Helene,Scalacci, Nicoloì,Petricci, Elena,Castagnolo, Daniele
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p. 5287 - 5295
(2015/05/27)
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- Gold-catalyzed reactions of propargylic esters with vinylazides for the synthesis of Z- or E-configured buta-1,3-dien-2-yl esters
-
Gold-catalyzed synthesis of buta-1,3-dien-2-yl esters by the reaction of propargyl esters with vinylazides is described; the reaction mechanism is postulated to involve a vinyl attack of vinylazides at alkenyl gold carbenes.
- Wagh, Sachin Bhausaheb,Liu, Rai-Shung
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supporting information
p. 15462 - 15464
(2015/10/20)
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- Diastereo- and enantioselective propargylation of benzofuranones catalyzed by pybox-copper complex
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Diastereo- and enantioselective preparation of 2,2-disubstituted benzofuran-3(2H)-one has been realized by a pybox-copper catalyzed reaction between 2-substituted benzofuran-3(2H)-one and propargyl acetate. The utility of this method was demonstrated by further transformation of the terminal alkyne into a methyl ketone without loss of enantiomeric purity.
- Zhao, Long,Huang, Guanxin,Guo, Beibei,Xu, Lijun,Chen, Jie,Cao, Weiguo,Zhao, Gang,Wu, Xiaoyu
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p. 5584 - 5587
(2015/02/19)
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- Stereocontrol in palladium-catalyzed propargylic substitutions: Kinetic resolution to give enantioenriched 1,5-enynes and propargyl acetates
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Kinetic resolution during the catalytic allyl-propargyl cross-coupling with chiral starting materials can be accomplished with a chiral palladium catalyst. These reactions offer ready access to enantiomerically enriched enyne products from simple, readily
- Ardolino, Michael J.,Eno, Meredith S.,Morken, James P.
-
supporting information
p. 3413 - 3419
(2013/12/04)
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- Silver(I)-catalyzed reaction between pyrazole and propargyl acetates: Stereoselective synthesis of the scorpionate ligands (E)-allyl-gem-dipyrazoles (ADPs)
-
The reaction between readily accessible pyrazole and propargyl acetates in the presence of Ag(I) catalyst yielded a new class of (E)-allyl-gem-dipyrazole scorpionate ligands: 1-aryl-2-N-pyrazolyl allyl acetates and 1,3-dipyrazolyl-3-arylpropene. The reaction showed broad substrate scope, and various functional and protecting groups were tolerated under the reaction conditions. The palladium(II) scorpionate complex could thus be easily prepared and successfully employed in Suzuki-Miyaura cross-couplings in water.
- Bhanuchandra,Kuram, Malleswara Rao,Sahoo, Akhila K.
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p. 11824 - 11834
(2014/01/06)
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- Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings
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The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.
- Ardolino, Michael J.,Morken, James P.
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supporting information; experimental part
p. 8770 - 8773
(2012/07/02)
-
- Enantioselective copper-catalysed propargylic substitution: Synthetic scope study and application in formal total syntheses of (+)-anisomycin and (-)-cytoxazone
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A copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic esters with different side chains (R=Ar, Bn, alkyl) into their amine counterparts in very high yields and with good enantioselectivities (up to 90% enantiomeric excess (ee)). Different amine nucleophiles were applied in the reactions and the highest enantioselectivities were obtained for aniline and its analogues. Interestingly, some carbon nucleophiles could also be used and with indoles excellent ee values were obtained (up to 98% ee). The versatility of the propargylic amines obtained was demonstrated by their further elaboration to formal total syntheses of the antibiotic (+)-anisomycin and the cytokine modulator (-)-cytoxazone. Copyright
- Detz, Remko J.,Abiri, Zohar,Le Griel, Remi,Hiemstra, Henk,Van Maarseveen, Jan H.
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experimental part
p. 5921 - 5930
(2011/06/26)
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- Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B
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A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.
- Ghosh, Nayan,Nayak, Sanatan,Sahoo, Akhila K.
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supporting information; experimental part
p. 500 - 511
(2011/04/17)
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- Highly diastereoselective synthesis of tetrahydrobenzofuran derivatives by?palladium-catalyzed reaction of propargylic esters with substituted β-dicarbonyl compounds
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Reactions of propargylic esters with 2-substituted cyclohexane-1,3-diones and 2-oxocyclohexanecarboxylic esters in the presence of palladium catalyst are described. Substituted tetrahydrobenzofuran derivatives having a quaternary carbon stereocenter were
- Yoshida, Masahiro,Higuchi, Mariko,Shishido, Kozo
-
experimental part
p. 2675 - 2682
(2010/05/18)
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- Reaction of difluorocarbene with propargyl esters and efficient synthesis of difluorocyclopropyl ketones
-
Difluorocarbene generated from FSO2CF2CO2SiMe3 (TFDA) at 120 °C could reacted with terminal alkynes having an ester group at the α position to the triple bond. Difluorocyclopropenes were further converted to difluorocyclopropyl ketones under alkaline condition. Mechanism for the conversion was studied.
- Hang, Xiao-Chun,Gu, Wei-Peng,Chen, Qing-Yun,Xiao, Ji-Chang
-
supporting information; experimental part
p. 6320 - 6324
(2009/12/09)
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- Asymmetrie copper-catalyzed propargylic substitution reaction of propargylic acetates with enamines
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Enamines served as carbon-nucleophiles for the first time In the Cu-catalyzed asymmetric propargylic substitution reaction of propargylic acetates, providing corresponding chiral β-ethynyl-substituted ketones In high yields and In good to high enantioselectivity.
- Fang, Ping,Hou, Xue-Long
-
supporting information; experimental part
p. 4612 - 4615
(2009/12/09)
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- Enantioselective copper-catalyzed propargylic amination
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(Chemical Equation Presented) A proper copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic acetates with aromatic side chains (R = Ar) into their amine counterparts in high yield and with good selectivity (up to 88% ee). The resulting chiral propargylic amines can be elaborated further into P,N ligands (see scheme; DIPEA = diisopropylethylamine).
- Detz, Remko J.,Delville, Marielle M. E.,Hiemstra, Henk,Van Maarseveen, Jan H.
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p. 3777 - 3780
(2008/12/23)
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- [(NHC)AuI]-catalyzed formation of conjugated enones and enals: An experimental and computational study
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The [(NHC)AuI]-catalyzed (NHC = N-heterocyclic carbene) formation of α,β-unsaturated carbonyl compounds (enones and enals) from propargylic acetates is described. The reactions occur at 60°C in 8 h in the presence of an equimolar mixture of [(NHC)AuCl] and AgSbF6 and produce conjugated enones and enals in high yields. Optimization studies revealed that the reaction is sensitive to the solvent, the NHC, and, to a lesser extent, to the silver salt employed, leading to the use of [(ItBu)AuCl]/ AgSbF6 in THF as an efficient catalytic system. This transformation proved to have a broad scope, enabling the stereoselective formation of (E)-enones and -enals with great structural diversity. The effect of substitution at the propargylic and acetylenic positions has been investigated, as well as the effect of aryl substitution on the formation of cinnamyl ketones. The presence or absence of water in the reaction mixture was found to be crucial. From the same phenylpropargyl acetates, anhydrous conditions led to the formation of indene compounds via a tandem [3,3] sigmatropic rearrangement/intramolecular hydroarylation process, whereas simply adding water to the reaction mixture produced enone derivatives cleanly. Several mechanistic hypotheses, including the hydrolysis of an allenol ester intermediate and SN2′ addition of water, were examined to gain an insight into this transformation. Mechanistic investigations and computational studies support [(NHC)AuOH], produced in situ from [(NHC)AuSbF6] and H 2O, instead of cationic [(NHC)AuSbF6] as the catalytically active species. Based on DFT calculations performed at the B3LYP level of theory, a full catalytic cycle featuring an unprecedented transfer of the OH moiety bound to the gold center to the C≡C bond leading to the formation of a gold-allenolate is proposed.
- Marion, Nicolas,Carlqvist, Peter,Gealageas, Ronan,De Fremont, Pierre,Maseras, Feliu,Nolan, Steven P.
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p. 6437 - 6451
(2008/02/13)
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- Cationic rhodium(I)/bisphosphane complex-catalyzed isomerization of secondary propargylic alcohols to α,β-enones
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We have determined that hydrogenated cationic Rh(I)/bisphosphane complexes are highly active catalysts for the isomerization of secondary propargylic alcohols to α,β-enones. A kinetic resolution of secondary propargylic alcohols proceeded with moderate selectivity with [Rh((R)-BINA-P)]OTf as a catalyst. Mechanistic studies revealed that the isomerization proceeds through intramolecular 1,3- and 1,2-hydrogen migration pathways. The isomerization of propargylic diol derivatives was also investigated, which revealed that 1,4-diketones, furans, and α,β-enones were obtained from 2-butyn-1,4-diol, 1-methoxy-2-butyn-4-ol, and 1-acetoxy-2-butyn-4-ol derivatives, respectively. Furthermore, chemoselectivity of the isomerization of an acetylenic diol was investigated, and preferential oxidation of a propargylic hydroxy group was observed. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Tanaka, Ken,Shoji, Takeaki,Hirano, Masao
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p. 2687 - 2699
(2008/02/08)
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- Ruthenium-catalyzed [1,n]-metallotropic shift (n = 3, 5) of alkynyl carbene complex intermediates
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Low-temperature oxygenation of copper(I) complexes of N,N,N-,N-tetraethylpropane-1,3-diamine yields solutions containing both μ-η2:η2-peroxodicopper(II) (P) and bis(μ-oxo)dicopper(III) (O) valence isomers. The P/O equilibrium positio
- Ohe, Kouichi,Fujita, Michinobu,Matsumoto, Hideyuki,Tai, Yugo,Miki, Koji
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p. 9270 - 9271
(2007/10/03)
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- Palladium-catalyzed silastannation of secondary propargylic alcohols and their derivatives
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A series of terminal propargylic alcohols and their derivatives were subjected to Pd-catalyzed silastannation. In all reactions, complete regio- and stereoselectivities were observed with the tributyltin moiety exclusively adding to the internal carbon of the triple bond in a cis fashion, including the first example of a diyne bis-silastannation. Silastannation reaction products could sequentially be protiodesilylated or iododestannylated, thus providing synthetic routes to 1,1-gem-disubstituted alkenylstannanes and iodides, respectively.
- Nielsen, Thomas E.,Le Quement, Sebastian Le,Tanner, David
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p. 1381 - 1390
(2007/10/03)
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- Kinetic resolution of propargylic and allylic alcohols by Candida antarctica lipase (Novozyme 435)
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A number of chiral propargylic and allylic alcohols were resolved by lipase-catalyzed kinetic resolution (Novozyme 435). In some cases the enantiomeric excess was high (up to >99%).
- Raminelli, Cristiano,Comasseto, Joao V.,Andrade, Leandro H.,Porto, Andre L.M.
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p. 3117 - 31722
(2007/10/03)
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- Aryl propargylic alcohols of high enantiomeric purity via lipase catalyzed resolutions
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A variety of substituted aryl propargylic alcohols were prepared via lipase catalyzed resolutions, the enantioselective hydrolysis of the corresponding esters being the method of choice.
- Waldinger, Claudia,Schneider, Manfred,Botta, Maurizio,Corelli, Federico,Summa, Vincenzo
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p. 1485 - 1488
(2007/10/03)
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- Hydrolytic Resolution of Tertiary Acetylenic Acetate Esters With the Lipase from Candida Cylindracea
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The kinetic resolution of a series of tertiary acetylenic acetate esters using the lipase from Candida cylindracea has been explored.Compounds 6c and the trifluoromethyl acetate 6e have been resolved with high enantiomeric enrichment.Several other tertiary acetate esters carrying a CF3 group have been investigated which proved inert to enzymatic hydrolysis.From these results and published data, we are able to propose a predictive model for identifying the preferred enantiomer of secondary and tertiary trifluoromethyl acetate esters for this lipase.
- O'Hagan, David,Zaidi, Naveed A.
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p. 947 - 949
(2007/10/02)
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- ENENTIOSELECTIVE HYDROLYSES BY BAKER'S YEAST - III. MICROBIAL RESOLUTION OF ALKYNYL ESTERS USING LYOPHILIZED YEAST
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Both enantiomers of optically active 1-alkyn-3-ols were obtained in high optical purity by microbial resolution of their racemic acetate using a stable ready-to-use lyophilized yeast preparation.
- Glaenzer, B. I.,Faber, K.,Griengl, H.
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p. 5791 - 5796
(2007/10/02)
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- Regiospecific Synthesis of a Terminal, Oxyfunctionalized Methyl Ketone Enamines via Catalytic Aminomercuriation of Prop-2-ynyl Esters and Ethers
-
Catalytic aminomercuriation of 1-substituted prop-2-ynyl esters and ethers (5) provides a mild, simple, and regiospecific route to the terminal functionalized enamines (6) despite the fact that they are potentially isomerisable to their internal form; hyd
- Barluenga, Jose,Aznar, Fernando,Liz, Ramon,Postigo, Carmen
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p. 1465 - 1467
(2007/10/02)
-