- Pd-Catalyzed Cascade Reactions of Aziridines: One-Step Access to Complex Tetracyclic Amines
-
The combination of palladium catalysis and thermal cycloaddition is shown to transform tricyclic aziridines into complex, stereodefined tetracyclic products in a single step. This highly unusual cascade process involves a diverted Tsuji-Trost sequence leading to a surprisingly facile intramolecular Diels-Alder reaction. The starting materials are accessible on multigram scales from the photochemical rearrangement of simple pyrroles. The tetracyclic amine products can be further elaborated through routine transformations, highlighting their potential as scaffolds for medicinal chemistry.
- Booker-Milburn, Kevin I.,Knowles, Jonathan P.,Latter, Francesca,Schwarz, Maria,Steeds, Hannah G.
-
supporting information
p. 4986 - 4990
(2021/07/19)
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- Facile synthesis of biarylmethanes and tetrasubstituted arenes: Via a base-mediated [3 + 3] benzannulation reaction of Morita-Baylis-Hillman adducts and unsaturated sulfones
-
A facile DBU-mediated [3 + 3] benzannulation reaction of 1,3-bis-sulfonyl propenes and Morita-Baylis-Hillman (MBH) bromides is described. The benzannulation reaction afforded bis-sulfonyl biarylmethanes/arenes with complete regioselectivity. The products
- Yadav, Deepak,Sharma, Sunil K.,Menon, Rajeev S.
-
p. 4073 - 4076
(2019/04/30)
-
- Amino acid ionic liquids as catalysts in a solvent-free Morita-Baylis-Hillman reaction
-
In the present work, we describe the preparation of ten amino acid ionic liquids (AAILs) formed from ammonium salts as cations, derivatives of glycerol, and natural amino acids as anions. All of them are viscous oils, colorless or pale yellow, and hygroscopic at room temperature. They have appreciable solubility in many protic and aprotic polar solvents. The AAILs were used as catalysts in a Morita-Baylis-Hillman (MBH) reaction. The ionic liquids derivative from l-proline and l-histidine demonstrated the ability to catalyze the reaction between methyl vinyl ketone and aromatic aldehydes differently substituted in the absence of an additional co-catalyst under organic solvent-free conditions. The AAIL derivatives from l-valine, l-leucine, and l-tyrosine catalyzed the MBH reaction only in the presence of imidazole. The MBH adducts were obtained in moderate to good yields. Although the catalytic site in the ILs was in its enantiomerically pure form, all the MBH adducts were obtained in their racemic form.
- Pereira, Mathias Prado,Souza Martins, Rafaela De,De Oliveira, Marcone Augusto Leal,Bombonato, Fernanda Irene
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p. 23903 - 23913
(2018/07/13)
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- Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates
-
The present study reports the organocatalytic enantioselective allylic amination of Morita–Baylis–Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Br?nsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.
- Do?ekal, Vojtěch,?imek, Michal,Dra?ínsky, Martin,Vesely, Jan
-
supporting information
p. 13441 - 13445
(2018/09/21)
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- A cascade synthesis of: S -allyl benzoylcarbamothioates via Mumm-type rearrangement
-
A catalyst and solvent free synthesis of S-allyl benzoylcarbamothioates has been achieved from the in situ generated benzoylcarbonimidothioates obtained by reacting MBH alcohols with aroyl isothiocyanates. An intramolecular thia-Michael addition of the in
- Dahiya, Anjali,Ali, Wajid,Alam, Tipu,Patel, Bhisma K.
-
supporting information
p. 7787 - 7791
(2018/11/21)
-
- Copper-Catalyzed Asymmetric 1,2-Addition of Grignard Reagents to 3-Acyl 2 H -chromenes
-
Enones in which the carbon-carbon double bond is part of the pharmacologically important 2 H -chromene (2 H -1-benzopyran) nucleus undergo asymmetric copper-catalyzed 1,2-addition of Grignard reagents. High yields and enantiomeric excesses up to 84% are o
- Calvo, Beatriz C.,Minnaard, Adriaan J.
-
p. 2624 - 2628
(2017/10/06)
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- Proline-Mediated Baylis-Hillman Reaction of Methyl Vinyl Ketone without a Co-catalyst under Solvent-Free Conditions
-
A proline-mediated Baylis-Hillman reaction of methyl vinyl ketone with aromatic aldehydes has been carried out without using any co-catalyst, under solvent-free conditions. The reaction works efficiently at 60 °C in the presence of a small amount of water
- Inani, Heena,Jha, Ajit Kumar,Easwar, Srinivasan
-
p. 128 - 132
(2016/12/26)
-
- A 2D Coordination Network That Detects Nitro Explosives in Water, Catalyzes Baylis-Hillman Reactions, and Undergoes Unusual 2D→3D Single-Crystal to Single-Crystal Transformation
-
The solvothermal reaction of Zn(NO3)2·6H2O and a linear dicarboxylate ligand H2L, in the presence of urotropine in N,N′-dimethylformamide (DMF), gives rise to a new porous two-dimensional (2D) coordination netwo
- Sharma, Vivekanand,De, Dinesh,Pal, Sanchari,Saha, Prithwidip,Bharadwaj, Parimal K.
-
supporting information
p. 8847 - 8855
(2017/08/14)
-
- Control of Chemo-, Regio-, and Enantioselectivity in Copper Hydride Reductions of Morita-Baylis-Hillman Adducts
-
Nonracemically ligated copper hydride can be used to effect tandem SN2′/1,2-reductions of racemic Morita-Baylis-Hillman (MBH) acetates to access enantioenriched chiral allylic alcohols with defined olefin geometry. MBH esters, including those w
- Linstadt, Roscoe T. H.,Peterson, Carl. A.,Jette, Carina I.,Boskovic, Zarko V.,Lipshutz, Bruce H.
-
supporting information
p. 328 - 331
(2017/04/21)
-
- A Porous Cu(II)-MOF with Proline Embellished Cavity: Cooperative Catalysis for the Baylis-Hillman Reaction
-
l-Proline has been covalently attached in a rigid linear ligand, H4L, having an isophthalate moiety at each terminal to form the chiral ligand, H4LPRO. This linker has been used for the construction of a porous MOF, LCuPRO
- De, Dinesh,Pal, Tapan K.,Bharadwaj, Parimal K.
-
supporting information
p. 6842 - 6844
(2016/07/27)
-
- Synthesis of Chiral α-Trifluoromethylamines with 2,2,2-Trifluoroethylamine as a "building Block"
-
The β-isocupreidine, a cinchonine derived alkaloid, catalyzed asymmetric SN2′-SN2′ reaction between N-2,2,2-trifluoroethylisatin ketimines and MBH type carbonates was realized in a simple and efficient way. A series of chiral α-trifl
- Li, Xiaoyuan,Su, Jinhuan,Liu, Zhourujun,Zhu, Yuanyuan,Dong, Zhenghao,Qiu, Shuai,Wang, Jiayi,Lin, Li,Shen, Zhiqiang,Yan, Wenjin,Wang, Kairong,Wang, Rui
-
supporting information
p. 956 - 959
(2016/03/15)
-
- An efficient synthesis of dihydrobenzo[c]azepines from Morita-Baylis-Hillman adducts via Pictet-Spengler reaction
-
Various dihydrobenzo[c]azepines were synthesized in good yields via Pictet-Spengler cyclization protocol from tosylamide derivatives of Morita-Baylis-Hillman adducts and 1,3,5-trioxane. The synthesis was carried out in the presence of easily removable mon
- Moon, Hye Ran,Kim, Su Yeon,Roh, Hwa Jung,Kim, Jae Nyoung
-
supporting information
p. 680 - 684
(2016/05/19)
-
- Multivalency as a key factor for high activity of selective supported organocatalysts for the Baylis-Hillman reaction
-
The polystyrene-supported N-alkylimidazole-based dendritic catalysts for the Baylis-Hillman reaction exhibit one of the strongest beneficial effects of multivalent architecture ever reported for an organocatalyst. The yields in the model reaction of methy
- Goren, Kerem,Karabline-Kuks, Jeny,Shiloni, Yael,Barak-Kulbak, Einav,Miller, Scott J.,Portnoy, Moshe
-
p. 1191 - 1197
(2015/03/05)
-
- Enatioselective Chalcogeno-Baylis-Hillman reaction of arylaldehydes with MVK and acrylates catalyzed by chiral thiepin-TiCl4 complex
-
In a rational chiral molecular design of chalcogenides, optically active thiepin with C2-symmetric chirality was synthesized from commercially available thiophene. Then enatioselective Chalcogeno-Baylis-Hillman reactions of arylaldehydes with methyl vinyl ketone (MVK) and acrylates were investigated in the presence of thiepin-Lewis acid complex. Finally, up to 64% ee was achieved in the presence of 0.2 equiv. of (S)-thiepin at 20°C. Enatioselective Chalcogeno-Baylis-Hillman reactions between benzaldehydes and acrylates were investigated in the presence of chiral thiepin-Lewis acid complex. Finally, up to 64% ee was achieved in the presence of 0.2 equiv. of (S)-thiepin at 20°C. Copyright
- Yin, Yan,Sun, Guofeng,Zhang, Heng,Zhou, Hong,Wu, Fanhong
-
p. 365 - 369
(2014/05/20)
-
- Organocatalytic enantioselective allylic alkylation of MBH carbonates with β-keto esters
-
The highly stereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with β-ketoesters catalysed by β-ICD is described. The corresponding products containing two adjacent quaternary and tertiary carbon centers were obtained in good yields with high diastereoselectivity (up to 10 : 1 dr) and enantioselectivity (up to 95% ee).
- Kamlar,Hybelbauerova,Cisarova,Vesely
-
supporting information
p. 5071 - 5076
(2014/07/08)
-
- Enantiodivergence in the reduction of α-methyl and α-halomethyl enones by microorganisms
-
Enones (Z)-3-methyl-(Z)-3-chloromethyl- and (Z)-3-bromomethyl-4-R-3-buten- 2-one (R = n-pentyl, phenyl, 2′- and 4′-chlorophenyl, 3′- and 4′-nitrophenyl, 4′-methoxyphenyl) were synthesized and subjected to reduction by the microorganisms Saccharomyces cerevisiae andGeotrichum candidum. Whereas the bioreduction of 3-methy-4-R-3-buten-2-ones afforded the corresponding (S)-4-R-3-methybutan-2-ones, the bioreduction of 3-chloromethyl- and 3-bromomethyl-4-R-3-buten-2-ones afforded the corresponding (R)-4-R-3-methybutan-2-ones.
- De Paula, Bruno R.S.,Zampieri, Davila S.,Rodrigues, J. Augusto R.,Moran, Paulo J.S.
-
p. 973 - 981
(2013/09/23)
-
- Morita-Baylis-Hillman reaction of benzaldehydes with methyl vinyl ketone at ambient temperature using cross-linked poly-4-vinylpyridine as a solid heterogeneous base catalyst in the presence of hydrogen peroxide
-
Morita-Baylis-Hillman (MBH) reaction of various aromatic aldehydes and methyl vinyl ketone (MVK) is effectively catalyzed by cross-linked poly-4-vinylpyridine (CPVP), a solid heterogeneous polymer-based base catalyst, in the presence of hydrogen peroxide
- Patil, Nitin R.,Kshirsagar, Siddheshwar W.,Samant, Shriniwas D.
-
p. 1703 - 1712
(2014/01/17)
-
- L-proline and L-histidine co-catalyzed Baylis-Hillman reaction
-
Baylis-Hillman reaction between an aldehyde and an activated alkene, such as alkyl vinyl ketones, acrylates, acrylonitrile, and vinylsulfones, giving the β-hydroxy-α-methylene carbonyl compounds, is a versatile and atom-economical carbon-carbon bond-formi
- Guo, Peng-Fei,Wei, Qing-Yi,Jiang, Hong,Xie, Peng-Fei
-
experimental part
p. 639 - 644
(2012/06/01)
-
- Regioselective carbon-carbon bond cleavage in the oxidation of cyclopropenylcarbinols
-
The strained double bond of cyclopropenylcarbinols undergoes a facile oxidation reaction to lead to unsaturated carbonyl derivatives. The distribution of the formed products depends on the relative stability of carbon-centered radical species, and the Sha
- Basheer, Ahmad,Mishima, Masaaki,Marek, Ilan
-
supporting information; experimental part
p. 4076 - 4079
(2011/10/04)
-
- Brucine N-oxide-catalyzed Morita-Baylis-Hillman reaction of vinyl ketones: A mechanistic implication of dual catalyst system with proline
-
The brucine N-oxide promoted Morita-Baylis-Hillman (MBH) reaction of vinyl ketones with aldehydes has been achieved. The corresponding asymmetric version of MBH reaction was also investigated, and the electron-deficient aryl aldehydes have emerged as suit
- Oh, Kyungsoo,Li, Jian-Yuan,Ryu, Jinhyang
-
scheme or table
p. 3015 - 3024
(2010/09/06)
-
- Auto-tandem catalysis: Facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition-elimination reaction
-
A catalytic domino reaction producing substituted 2-alkylidenecyclohexanone from 3-oxymethyl-2-siloxy-1,3-butadienes, which can be prepared from Baylis-Hillman adducts, and α,β-unsaturated ketones is described. The process involves two mechanistically dis
- Takasu, Kiyosei,Tanaka, Toru,Azuma, Takumi,Takemoto, Yoshiji
-
scheme or table
p. 8246 - 8248
(2010/12/20)
-
- Reaction of Baylis-Hillman adducts with fluorinated silanes
-
Reactions of acylated Baylis-Hillman adducts bearing nitrile, ester, or ketone groups with C6F5-substituted silicon reagents MenSi(C6F5)4-n (n = 1-3) have been studied. The reactions are in
- Zemtsov, Artem A.,Levin, Vitalij V.,Dilman, Alexander D.,Struchkova, Marina I.,Belyakov, Pavel A.,Tartakovsky, Vladimir A.,Hu, Jinbo
-
supporting information; scheme or table
p. 6779 - 6785
(2011/03/19)
-
- N-alkylimidazole as amphiphilic organocatalyst: 'Catalytic' Morita-Baylis-Hillman reaction on water without organic solvent
-
In the presence of water, a Morita-Baylis-Hillman reaction between methyl vinyl ketone and various aldehydes was performed with a catalytic amount of an imidazole carrying a hydrophobic group. Georg Thieme Verlag Stuttgart.
- Asano, Keisuke,Matsubara, Seijiro
-
experimental part
p. 35 - 38
(2009/05/27)
-
- Morita-baylis-hillman reaction on water without organic solvent, assisted by a 'catalytic' amount of amphiphilic imidazole derivatives
-
A Morita-Baylis-Hillman (MBH) reaction using water as a solvent without any organic solvent can be performed by using an amphiphilic N-alkylimidazole. This reaction is accelerated by the addition of water and is the first example of a 'catalytic' MBH reaction without organic solvent in the presence of water.
- Asano, Keisuke,Matsubara, Seijiro
-
experimental part
p. 3219 - 3226
(2010/02/28)
-
- Selenonium ionic liquid as efficient catalyst for the Baylis-Hillman reaction
-
The new acidic ionic liquid phenyl butyl ethyl selenonium tetrafluoroborate, [pbeSe]BF4, was successful used as a co-catalyst in the Baylis-Hillman reaction of aldehydes and electron-deficient alkenes. The Baylis-Hillman adducts were obtained i
- Lenard?o, Eder J.,Feijó, Josiane de Oliveira,Thurow, Samuel,Perin, Gelson,Jacob, Raquel G.,Silveira, Claudio C.
-
experimental part
p. 5215 - 5217
(2009/12/06)
-
- First evidence of proline acting as a bifunctional catalyst in the Baylis-Hillman reaction between alkyl vinyl ketones and aryl aldehydes
-
Proline in the presence of sodium hydrogen carbonate has been found to be an effective catalyst for the Baylis-Hillman reaction between methyl or ethyl vinyl ketone and aryl aldehydes. Screening of several amine catalysts showed that an ionizable carboxyl
- Gruttadauria, Michelangelo,Giacalone, Francesco,Lo Meo, Paolo,Marculescu, Adriana Mossuto,Riela, Serena,Noto, Renato
-
scheme or table
p. 1589 - 1596
(2009/04/11)
-
- A novel ytterbium/perfluoroalkylated-pyridine catalyst for Baylis-Hillman reaction in a fluorous biphasic system
-
Ytterbium perfluorooctanesulfonate [Yb(OPf)3] catalyses the highly efficient Baylis-Hillman reaction in the presence of a catalytic amount of a novel perfluoroalkylated-pyridine as a ligand in a fluorous biphasic system (FBS) composed of toluen
- Yi, Wen-Bin,Cai, Chun,Wang, Xin
-
p. 919 - 924
(2008/03/14)
-
- Bifunctional polymeric organocatalysts and their application in the cooperative catalysis of Morita-Baylis-Hillman reactions
-
A series of soluble, noncross-linked polystyrene-supported tri-phenylphosphane and 4-dimethylaminopyridine reagents were prepared. Some of these polymeric reagents contained either alkyl alcohol or phenol groups on the polymer backbone. The use of these materials as organocatalysts in a range of Morita-Baylis-Hillman reactions indicated that hydroxyl groups could participate in the reactions and accelerate product formation. In the cases examined, phenol groups were more effective than alkyl alcohol groups for catalyzing the reactions. This article is one of the first reports of the synthesis and use of non-natural, bifunctional polymeric reagents for use in organic synthesis in which both functional groups can cooperatively participate in the catalysis of reactions.
- Kwong, Cathy Kar-Wing,Huang, Rui,Zhang, Minjuan,Shi, Min,Toy, Patrick H.
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p. 2369 - 2376
(2008/02/02)
-
- Enantioselective allylic substitution of Morita-Baylis-Hillman adducts catalyzed by planar chiral [2.2]paracyclophane monophosphines
-
Planar chiral [2,2]cyclophane monophosphines are efficient catalyst in the reaction of Morita-Baylis-Hillman adducts with phthalimide. The corresponding allylic substituted products were afforded in high yields and in good to moderate ee.
- Zhang, Tang-Zhi,Dai, Li-Xin,Hou, Xue-Long
-
p. 1990 - 1994
(2008/02/13)
-
- The first air-stable and efficient nucleophilic trialkylphosphine organocatalyst for the Baylis-Hillman reaction
-
1,3,5,-Triaza-7-phosphaadamantane (PTA) is first reported to be a convenient and efficient nucleophilic trialkylphosphine organocatalyst for the Baylis-Hillman reaction. Thus, under the mediation of 15-20 mol % of PTA and practical conditions, both aromat
- He, Zhengrong,Tang, Xiaofang,Chen, Yaoming,He, Zhengjie
-
p. 413 - 417
(2007/10/03)
-
- Traditional Morita-Baylis-Hillman reaction of aldehydes with methyl vinyl ketone co-catalyzed by triphenylphosphine and nitrophenol
-
The development of a chiral Broonsted acid-catalyzed asymmetric Morita-Baylis-Hilman reaction of cyclone with aldehyde in the presence of triethyphosphine (PE3) was analyzed using nuclear magnetic resonance (NMR). Another catalytic system for t
- Shi, Min,Liu, Ying-Hao
-
p. 1468 - 1470
(2008/02/03)
-
- Dialkylaminopyridine-functionalized mesoporous silica nanosphere as an efficient and highly stable heterogeneous nucleophilic catalyst
-
A new nucleophilic catalytic system comprised of dialkylaminopyridine- functionalized mesoporous silica nanosphere (DMAP-MSN) has been synthesized and characterized. We have demonstrated that this material is an efficient heterogeneous catalyst for Baylis-Hillman, acylation, and silylation reactions with good reactivity, product selectivity, and recyclability. We envision that this DMAP-functionalized mesoporous silica material can also serve as an effective heterogeneous catalyst for many other catalytic nucleophilic reactions.
- Chen, Hung-Ting,Huh, Seong,Wiench, Jerzy W.,Pruski, Marek,Lin, Victor S.-Y.
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p. 13305 - 13311
(2007/10/03)
-
- Poly(ethyleneglycol) (PEG): A rapid and recyclable reaction medium for the DABCO-catalyzed Baylis-Hillman reaction
-
PEG (400) has been used as a rapid and recyclable reaction medium for the Baylis-Hillman reaction with the conventional basic catalyst DABCO (20mol%) with very good yields of products. Recyclability is achieved with no further addition of DABCO to the rea
- Chandrasekhar,Narsihmulu, Ch.,Saritha,Shameem Sultana
-
p. 5865 - 5867
(2007/10/03)
-
- Sulpholane - A new solvent for the Baylis-Hillman reaction
-
Sulpholane, a commercially available solvent, is used for the first time as a new solvent for the Baylis-Hillman reaction under ambient conditions; a wide variety of olefins as well as aldehydes participate very efficiently resulting in good to excellent
- Krishna, Palakodety Radha,Manjuvani,Kannan,Sharma
-
p. 1183 - 1185
(2007/10/03)
-
- Acceleration of the DABCO-promoted Baylis-Hillman reaction using a recoverable H-bonding organocatalyst
-
It has been shown that catalytic amounts (20-40mol%) of bis-aryl (thio)ureas greatly accelerate the DABCO-promoted Baylis-Hillman reaction between a range of aromatic aldehydes and methyl acrylate in the absence of solvent. These robust organocatalysts ar
- Maher, Declan J.,Connon, Stephen J.
-
p. 1301 - 1305
(2007/10/03)
-
- Novel application of phosphonium salts as co-catalysts for the Baylis-Hillman reaction
-
Excellent yields have been obtained when the Baylis-Hillman reaction is conducted in the presence of phosphonium salts.
- Johnson, Claire L.,Donkor, Rachel E.,Nawaz, Wafaa,Karodia, Nazira
-
p. 7359 - 7361
(2007/10/03)
-
- A Highly Active and Selective Catalyst System for the Baylis-Hillman Reaction
-
A key role for sulfur and the potential for Nax→P intrabridgehead interactions are invoked to explain the impressive effect of the cocatalyst (shown in color) in the TiCl4-mediated Baylis-Hillman reaction [Eq. (1)]. Even sterically h
- You, Jingsong,Xu, Juhua,Verkade, John G.
-
p. 5054 - 5056
(2007/10/03)
-
- Reexamination of the traditional Baylis-Hillman reaction
-
In the Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone (MVK), we found that, besides the normal Baylis-Hillman adduct 1, the diadduct 2 can also be formed at the same time and the yield of 2 can reach to 55% if increasing the amount of methyl vinyl ketone. But for ethyl vinyl ketone (EVK), methyl acrylate or acrylonitrile, only the normal Baylis-Hillman adduct 4, 7 or 8 was obtained, respectively. The substituent's effects and Lewis base effects were also examined and a plausible reaction mechanism was proposed for the formation of 2.
- Shi, Min,Li, Chao-Qun,Jiang, Jian-Kang
-
p. 1181 - 1189
(2007/10/03)
-
- The Baylis-Hillman reactions of aldehydes with methyl vinyl ketone in the presence of imidazole, binol and silica gel
-
In the Baylis-Hillman reaction of aldehydes with methyl vinyl ketone, we found that, in the presence of a stoichiometric amount of binol and silica gel (SiO2), a weak Lewis base such as imidazole can promote the reaction to give the normal Bayl
- Shi, Min,Jiang, Yuan
-
p. 564 - 566
(2007/10/03)
-
- Polymer-Supported Lewis Bases for the Baylis-Hillman Reaction
-
The use of polymer-supported Lewis bases such as PEG4600- (PPh2)2 and poly(DMAP) in the Baylis-Hillman reactions of N-tosylimines (ArCH=NTs) 1 or the corresponding arenecarbaldehydes with α,β-unsaturated ketones has been i
- Huang, Jin-Wen,Shi, Min
-
p. 953 - 958
(2007/10/03)
-
- Heterogeneous Baylis-Hillman using a polystyrene-bound 4-(N-benzyl-N- methylamino)pyridine as reusable catalyst
-
An insoluble Merrifield type resin having 4-aminopyridine units is a suitable and reusable heterogeneous catalyst for the Baylis-Hillman coupling of aromatic aldehydes and α,β-unsaturated ketones.
- Corma, Avelino,Garcia, Hermenegildo,Leyva, Antonio
-
p. 2806 - 2807
(2007/10/03)
-
- The Baylis-Hillman reaction under high pressure induced by water-freezing
-
High pressure (about 200 MPa), which was realized by freezing water in a sealed autoclave, has been successfully applied to the Baylis-Hillman reaction, in which an efficient rate enhancement was observed.
- Hayashi, Yujiro,Okado, Kotaro,Ashimine, Itaru,Shoji, Mitsuru
-
p. 8683 - 8686
(2007/10/03)
-
- Sulfide-BF3·OEt2 mediated Baylis-Hillman reactions
-
A sulfide-BF3·OEt2 mediated Baylis-Hillman reaction has been developed in which the sulfide acts via attack onto the activated alkene. The use of a chiral sulfide gives rise to Baylis-Hillman adducts with up to 53% ee.
- Walsh, Louise M.,Winn, Caroline L.,Goodman, Jonathan M.
-
p. 8219 - 8222
(2007/10/03)
-
- Lewis base and L-proline co-catalyzed Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone
-
In the Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone, we found that, in the presence of a catalytic amount of L-proline, weak Lewis bases such as imidazole and triethylamine as well as the stronger Lewis base DABCO, can promote the Bay
- Shi, Min,Jiang, Jian-Kang,Li, Chao-Qun
-
p. 127 - 130
(2007/10/03)
-
- Dimethyl sulfide-boron trihalide-mediated reactions of α,β-unsaturated ketones with aldehydes: One-pot synthesis of Baylis-Hillman adducts and α-halomethyl enones
-
The reactions of aldehydes with 3-buten-2-one (2) were conducted in the presence of BBr3·Me2S or BCl3·Me2S and then worked up with aqueous NaHCO3, affording the α-methylene aldol 3, α-halomethyl aldol 4 or 6, and α-halomethyl enones 5 or 7, respectively. In contrast, the reactions quenched with water gave the α-halomethyl enones 5 or 7 in high yields, while the work-up with an aqueous 10% trimethylamine gave the α-methylene aldol 3. The phenol 15 and half-acetal 16 were obtained from the reaction of p-nitrobenzaldehyde (1a) with cyclohexenone (10).
- Iwamura, Tatsunori,Fujita, Masaru,Kawakita, Tetsuya,Kinoshita, Sayaka,Watanabe, Shin-Ichi,Kataoka, Tadashi
-
p. 8455 - 8462
(2007/10/03)
-
- New discovery in the traditional Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone
-
In the Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone, we found that, besides the normal Baylis-Hillman reaction product 1, the diadduct 2 can also be formed at the same time and the yield of 2 can reach 55% by increasing the amount of
- Shi,Li,Jiang
-
p. 833 - 834
(2007/10/03)
-
- Stereoselective transformation of Baylis-Hillman adducts into (3E)-3- (alkoxymethyl)alk-3-en-2-ones
-
The pure (3E)-3-(methoxymethyl)alk-3-en-2-ones and (3E)-3- (ethoxymethyl)alk-3-en-2-ones are formed in the acid induced reaction of 4- hydroxy-3-methylenealkan-2-ones with methanol and ethanol, respectively.
- Basavaiah, Deevi,Suguna Hyma, Rachakonda,Muthukumaran, Kannan,Kumaragurubaran, Nagaswamy
-
p. 217 - 219
(2007/10/03)
-
- Synthetic applications of the Baylis-Hillman adducts: A simple stereoselective synthesis of (E)-3-(nitroxymethyl)alk-3-en-2-ones
-
First simple, stereoselective synthesis of (E)-3-(nitroxymethyl)alk-3-en-2-ones from Baylis-Hillman adducts (4-hydroxy-3-methylenealkan-2-ones) is described. (C) 2000 Elsevier Science Ltd.
- Basavaiah, Deevi,Suguna Hyma, Rachakonda,Kumaragurubaran, Nagaswamy
-
p. 5905 - 5907
(2007/10/03)
-
- An improved vinylalumination procedure replacing HMPA with NMO for the hydroalumination of α-acetylenic esters and ketones
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Replacing carcinogenic HMPA with NMO, a higher yielding, enviornmentally benign procedure for the vinylalumination of carbonyl compounds with [α-(ethoxycarbonyl)vinyl]diisobutylaluminium and its β-methyl or -phenyl analogs, as well as [α-(acetyl)vinyl]dii
- Ramachandran, P. Veeraraghavan,Reddy, M. Venkat Ram,Rudd, Michael T.
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p. 1979 - 1980
(2007/10/03)
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- 2,6-diphenyl-4H-chalcogenopyran-4-ones and 2,6-diphenyl-4H- chalcogenopyran-4-thiones: A new catalyst for the Baylis-Hillman reaction
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2,6-Diphenyl-4H-chalcogenopyran-4-ones and 2,6-diphenyl-4H- chalcogenopyran-4-thiones, a new series of catalysts for the Baylis-Hillman reaction, were investigated. The reactions proceeded smoothly in the presence of 1 mol eq. of TiCl4 under at
- Iwama, Tetsuo,Kinoshita, Hironori,Kataoka, Tadashi
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p. 3741 - 3744
(2007/10/03)
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