cas 78385-36-1, (Benzyloxycarbonylmethyl)triphenylphosphonium bromide

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Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates
A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E -selectivity.
Liu, Teng,He, Chixian,Wang, Fan,Shen, Xiang,Li, Yongqin,Lang, Man,Li, Guijun,Huang, Chao,Cheng, Feixiang
p. 518 - 526
(2020/10/12)

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides
Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).
Liu, Xin,Werner, Thomas
supporting information
p. 1096 - 1104
(2020/12/31)

DMAP Mediated Efficient Construction of Functionalized Chromenes through One-Pot Reaction of para-Quinone Methides with Allenoates
A novel DMAP-mediated Rauhut-Currier/oxa-Michael addition cascade reaction of hydroxylphenyl-substituted para-quinone methide with allenoate was reported for the first time. A series of functionalized chromenes were successfully obtained with moderate to
Song, Zefeng,Jia, Yuping,Zhang, Daizhou,Wang, De
supporting information
p. 1942 - 1948
(2021/04/05)

Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones
An efficient enantioselective [3+2] cycloaddition of isomünchnones with methyleneindolinones that are generated by anin situintramolecular addition of the carbonyl group to rhodium carbenes is realized with a chiralN,N′-dioxide/Zn(ii) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values.
Feng, Xiaoming,Hu, Xinyue,Lin, Lili,Wang, Kaixuan,Xu, Chaoran,Zhou, Yuqiao
supporting information
p. 8917 - 8920
(2021/09/10)

Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.
Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.
supporting information
p. 9413 - 9418
(2021/12/09)

Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts
Herein we report the first highly enantioselective allenoate-Claisen rearrangement using doubly axially chiral phosphate sodium salts as catalysts. This synthetic method provides access to β-amino acid derivatives with vicinal stereocenters in up to 95percent ee. We also investigated the mechanism of enantioinduction by transition state (TS) computations with DFT as well as statistical modeling of the relationship between selectivity and the molecular features of both the catalyst and substrate. The mutual interactions of charge-separated regions in both the zwitterionic intermediate generated by reaction of an amine to the allenoate and the Na+-salt of the chiral phosphate leads to an orientation of the TS in the catalytic pocket that maximizes favorable noncovalent interactions. Crucial arene-arene interactions at the periphery of the catalyst lead to a differentiation of the TS diastereomers. These interactions were interrogated using DFT calculations and validated through statistical modeling of parameters describing noncovalent interactions.
Ellwart, Mario,Gensch, Tobias,Han, Seo-Jung,Lin, Hsin-Hui,Miró, Javier,Sigman, Matthew S.,Toste, F. Dean
supporting information
p. 6390 - 6399
(2020/04/27)

SUBSTITUTED PYRROLIDINES AND THEIR USE
The invention discloses compounds of Formula (I) wherein R1, R2, R3, R3A, R4, and R5 are as defined herein. The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the invention.
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Paragraph 0330

(2019/10/30)

NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ-Functionalized Allenoates
An N-heterocyclic carbene (NHC) catalyzed γ-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the γ-adduct was more energetically favorable than that of the α-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.
Li, Sha,Tang, Ziwei,Wang, Yang,Wang, Dan,Wang, Zhanlin,Yu, Chenxia,Li, Tuanjie,Wei, Donghui,Yao, Changsheng
supporting information
p. 1306 - 1310
(2019/02/26)

Phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles and allenoates
The efficient phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles with allenoates has been successfully developed, providing a facile access to cyclopenta[b]indolines with good to excellent yields and high diastereoselectivities. This strategy features mild reaction conditions, high functional group tolerance, and scalability. Additionally, the 2-nitrobenzofuran and 2-nitrobenzothiophene were good dearomative [3+2] annulation partners.
Liu, Kui,Wang, Gang,Cheng, Shao-Jie,Jiang, Wen-Feng,He, Cheng,Ye, Zhi-Shi
supporting information
p. 1885 - 1890
(2019/06/21)

A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions
A Ba/Pd cooperative catalysis system was developed to enable the dehydrative cross-coupling of allylic alcohols with P-ylides to occur directly and promote a subsequent Wittig reaction in one pot. A variety of multisubstituted 1,4-dienes were isolated in good to excellent yields with broad P-ylides (stabilized by both ester and ketone carbonyl groups) and aldehyde (aliphatic and aromatic) substrates with excellent E selectivity.
Xie, Peizhong,Fu, Weishan,Cai, Xinying,Sun, Zuolian,Wu, Ying,Li, Shuangshuang,Gao, Cuiqing,Yang, Xiaobo,Loh, Teck-Peng
supporting information
p. 7055 - 7059
(2019/09/12)

Allenoate Prenucleophiles: A Triply Diastereoselective Approach to β-Hydroxy Esters Containing All-Carbon α-Quaternary Centers
Allenyl esters activated by titanium(IV) underwent additions to a wide range of aldehydes in high regio- and diastereoselectivities leading to products containing an all-carbon quaternary center bearing an α-vinyl group that was installed with high select
Maki, Samantha L.,Maity, Pradip,Dougherty, Shannon,Johns, Jennifer,Lepore, Salvatore D.
supporting information
p. 7952 - 7955
(2019/10/11)

Synthesis, crystal structural study and catalyst active of benzyloxycarbonylmethyl triphenylphosphonium hexabromopalladate (II) in amination of aryl halides and Suzuki cross-coupling reaction
In this study, palladium (II) chloride reacted with the phosphonium salt [PhCH2COOCH2P(Ph)3]Br to give [PhCH2COOCH2P(Ph)3]2[Pd2Br6] (1). The characterization of synthesized compound was performed by elemental analysis, FT-IR, 1H, 31P, 13C NMR and also X-ray crystallography. It was found that this compound works as an efficient catalyst for the amination of aryl halides to afford primary amines, the results of which were satisfactory. Furthermore, it was found that the catalyst showed a high activity for Suzuki carbon–carbon cross-coupling of aryl halides and phenylboronic acid. Interestingly, the catalyst can be recovered from the reaction mixture and recycled four consecutive runs without any significant loss in activity.
Ghorbani-Choghamarani, Arash,Naghipour, Ali,Babaee, Heshmatollah,Heidarnezhad, Hayedeh,Notash, Behrouz
p. 2123 - 2134
(2018/07/31)

A Tunable Route to Prepare α,β-Unsaturated Esters and α,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides
A tunable strategy to prepare α,β-unsaturated esters and α,β-unsaturated-γ-keto esters in good to excellent yields was developed through copper-catalyzed oxidative coupling of phosphorus ylides with alkenyl boronic acids under mild conditions. The reaction without water afforded α,β-unsaturated esters, ketones, and amides while α,β-unsaturated-γ-keto esters, 1,4-α,β-unsaturated diketones and α,β-unsaturated-γ-keto amides were obtained when using 5.0 equiv. of water. H2O18 labeling experiments showed that water played an important role in the formation of α,β-unsaturated-γ-keto esters. A plausible formation mechanism for α,β-unsaturated esters and α,β-unsaturated-γ-keto esters was proposed based on mechanistic studies. Phosphonium salts could also be used directly as coupling partners instead of phosphorus ylides. The reaction exhibited a broad substrate scope, good functional group tolerance, good regioselectivity, and diverse coupling products. (Figure presented.).
Bi, Hong-Yan,Liu, Feng-Ping,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
supporting information
p. 1510 - 1516
(2018/03/05)

Regio- and Stereoselective Nickel-Catalyzed Coupling of Boronic Acids with Allenoates
The Ni(II)-catalyzed cross-coupling of arylboronic acids with allenoates is documented. The high regio- and stereoselectivity of the process enables a wide range of β-aryl β,γ-unsaturated esters to be prepared in good to excellent yields (up to 95%) and high E / Z -selectivity. Additionally, [3+2]-cascade sequence was observed when 2-formylphenylboronic acid was employed.
Liu, Yang,Daka, Mario,Bandini, Marco
p. 3187 - 3196
(2018/08/17)

Substituted Pyrrolidines and Methods of Use
The invention discloses compounds of Formula (I) wherein R1, R2, R2A, R3, R3A, R4, R4A, and R5 are as defined herein. The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the invention.
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Paragraph 2179

(2018/04/20)

MACROCYCLIC INHIBITORS OF FLAVIVIRIDAE VIRUSES
Provided are compounds of Formula I: and pharmaceutically acceptable salts and esters thereof. The compounds, compositions, and methods provided are useful for the treatment of virus infections, particularly hepatitis C infections.
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Paragraph 0455

(2017/08/01)

Regio- and Stereoselective Copper(II)-Catalyzed Hydrosilylation of Activated Allenes in Water: Access to Vinylsilanes
By using catalytic amounts of copper(II), 4-picoline, and dimethylphenylsilylpinacol borane, a series of allenoates were silylated on the β carbon in good to excellent yields and high (E)-selectivity. The mild and efficient silylation method is conducted in water under atmospheric conditions to afford vinylsilanes.
Pashikanti, Srinath,Calderone, Joseph A.,Nguyen, Matthew K.,Sibley, Christopher D.,Santos, Webster L.
supporting information
p. 2443 - 2446
(2016/06/09)

Efficient and regioselective one-pot synthesis of S-vinyl dithiocarbamates from electron-deficient allenes, amines and CS2
A novel and efficient one-pot procedure for the synthesis of S-vinyl dithiocarbamates from electron-deficient allenes, amines and CS2was presented. The reactions proceed at room temperature for 10–30?min without any catalyst to afford the products in high yields, excellent regioselectivity and stereoselectivity.
Li, Ridong,Leng, Penglin,Liu, Bin,Wang, Xin,Ge, Zemei,Li, Runtao
supporting information
p. 5707 - 5712
(2016/08/23)

MACROCYCLIC INHIBITORS OF FLAVIVIRIDAE VIRUSES
Provided are compounds of Formula I: and pharmaceutically acceptable salts and esters thereof. The compounds, compositions, and methods provided are useful for the treatment of virus infections, particularly hepatitis C infections.
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Page/Page column 166

(2014/01/08)

Edge-Shared [M2Cl10]2- complexes of reaction between oxophilic group 4 metal and phosphorus ylides1
The reactions between oxophilic group 4 metal chlorides, α-keto ylides in THF, led to the forma-tion of titanium, zirconium and hafnium edge-shared [M2Cl10]2- complexes (1a-3f). We describe that the reaction between MClsu
Sabounchei,Ahmadi,Shahriari,Hoseini-Fashami,Samiee
experimental part
p. 1005 - 1013
(2012/10/08)

Allene carboxylates as dipolarophiles in Rh-catalyzed carbonyl ylide cycloadditions
Face-to-face: Allene carboxylates can serve as efficient dipolarophiles for Rh-catalyzed carbonyl ylide cycloadditions (see scheme). The endo and exo products arise from cycloaddition on the same face of the allene, but opposite faces of the dipole. This facial selectivity results in the formation of two of the four possible diastereomers.
Rout, Laxmidhar,Harned, Andrew M.
supporting information; experimental part
p. 12926 - 12928
(2010/05/19)

Thermal decomposition of triphenylphosphonium alkyl ester salts
In thermolyses of molten triphenylphosphonium alkyl ester bromides and chlorides, alkyl = methyl, ethyl, isopropyl, at 130 and 225°C, initial attack of the halide ion on the methyl group gives the methyl halide and ylid 1, Ph3P = CH2, which can be methylated, or is protonated by the phosphonium salt with transylidation giving Ph3P+-CH3X-, X = Br, Cl. The initial reactions of the ethyl or isopropyl esters are with the halide ion, X-, as a base giving ylid, 1, which can be protonated by HX or by transylidation. The t-butyl ester generates Ph3P+-CH3X-but no products of transylidation. The first-formed ylid1, can be trapped by reactive alkyl and acyl halides, and the transient ylidic esters decompose thermally to triphenyl phosphine oxide, Ph3P = O, react further with unreacted phosphonium ester, or are trapped by added aldehyde in a Wittig reaction. The final product compositions are affected by a decrease in pressure, due to escape of volatile intermediates, and by replacement of the X- halide ion by the less nucleophilic and basic tosylate ion. Reactions under reflux, in solution in chloroform, or in suspension in benzene, are similar to those of the molten salts, but yields are generally lower at the lower temperatures. Copyright Taylor & Francis Group, LLC.
Castaneda, Fernando,Aliaga, Christian,Acuna, Cristina,Silva, Paul,Bunton, Clifford A.
experimental part
p. 1188 - 1208
(2009/04/16)

Rapid and efficient access to meso-2,5-cis-disubstituted pyrrolidines by double aza-Michael reactions of chiral primary amines
The double aza-Michael reaction of enantiopure primary amines on bis α,β-unsaturated diesters has been studied under various activating conditions. High pressure allowed a rapid and efficient access to meso-2,5-disubstituted pyrrolidines.
Cabral dos Santos, Leila,Bahlaouan, Zineb,El Kassimi, Khadija,Troufflard, Claire,Hendra, Frederic,Delarue-Cochin, Sandrine,Zahouily, Mohamed,Cave, Christian,Joseph, Delphine
experimental part
p. 751 - 768
(2009/09/25)

An application of the phosphine-catalyzed [4 + 2] annulation in indole alkaloid synthesis: Formal syntheses of (±)-alstonerine and (±)-macroline
(Chemical Equation Presented) An application of the phosphine-catalyzed [4 + 2] annulation in the formal synthesis of alstonerine and macroline is reported. A phosphine-catalyzed [4 + 2] reaction between imine 7a and allene 8 formed the D ring of the targ
Tran, Yang S.,Kwon, Ohyun
p. 4289 - 4291
(2007/10/03)

The Chemistry of 4-Mercaptoazetidin-2-ones. Part 3. Synthesis of 6-Phenoxyacetamido-2-alkylidenepenam-3-carboxylic Acids
A general method for the preparation of α-bromoallenic esters (2) involving the reaction of an acid chloride with a carboxybromomethylenetriphenylphosphorane has been developed.Reaction of these esters with the 4-mercaptoazetidin-2-one (1) gave rise to the 2-alkylidenepenam esters (3).The title compounds, obtained by hydrogenolysis of the corresponding benzyl esters, showed only moderate antibacterial properties.
Osborne, Neal F.
p. 1429 - 1434
(2007/10/02)