Catalytic Asymmetric Michael Reactions of α,β-Unsaturated Ketones with Sulfonyl-Containing Nucleophiles: Chiral Synthesis of (R)-Muscone and (S)-Celery Ketone

被引：35

作者：

Sun, Xiaomin ^{[1
]}

Yu, Feng ^{[1
]}

Ye, Tingting ^{[1
]}

Liang, Xinmiao ^{[1
]}

Ye, Jinxing ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Minist Educ, Engn Res Ctr Pharmaceut Proc Chem, Shanghai 200237, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 02期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; ketones; Michael reactions; organocatalysis; sulfur; ENANTIOSELECTIVE ORGANOCATALYTIC ADDITION; CONJUGATE ADDITION; VINYL SULFONES; ALDEHYDES; CHEMISTRY; FLUOROBIS(PHENYLSULFONYL)METHANE; ALKYL; SULFONAMIDES; CLEAVAGE; ALKENYL;

D O I：

10.1002/chem.201002418

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An amine worth its salt: A highly enantioselective Michael addition reaction of α,β-unsaturated ketones with the sulfonyl-containing nucleophiles bis(phenylsulfonyl)methane and 1-(phenylsulfonyl)propan-2-one, catalyzed by a chiral primary amine salt, has been developed and gives excellent enantioselectivities (see scheme). The methodology has successfully demonstrated its synthetic utility in the chiral synthesis of (R)-muscone and (S)-celery ketone. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：430 / 434

页数：5

共 67 条

[11] Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones
Bartoli, Giuseppe
Bosco, Marcella
Carlone, Armando
Pesciaioli, Fabio
Sambri, Letizia
Melchiorre, Paolo
[J]. ORGANIC LETTERS, 2007, 9 (07) : 1403 - 1405
[12] Enantioselective routes to (-)-(R)-muscone
Bulic, Bruno
Luecking, Ulrich
Pfaltz, Andreas
[J]. SYNLETT, 2006, (07) : 1031 - 1034
[13] The development of asymmetric primary amine catalysts based on cinchona alkaloids
Chen, Ying-Chun
[J]. SYNLETT, 2008, (13) : 1919 - 1930
[14] Deng L., 2008, ANGEW CHEM, V120, P7824
[15] Evolving Organic Synthesis Fostered by the Pluripotent Phenylsulfone Moiety
El-Awa, Ahmad
Noshi, Mohammad N.
du Jourdin, Xavier Mollat
Fuchs, Philip L.
[J]. CHEMICAL REVIEWS, 2009, 109 (06) : 2315 - 2349
[16] Enders D, 2000, EUR J ORG CHEM, V2000, P879
[17] Fukuzumi T., 2006, ANGEW CHEM, V118, P5095
[18] Fluorobis(phenylsulfonyl)methane: A fluoromethide equivalent and palladium-catalyzed enantioselective allylic monofluoromethylation
Fukuzumi, Takeo
Shibata, Norio
Sugiura, Masayoshi
Yasui, Hiroyuki
Nakamura, Shuichi
Toru, Takeshi
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) : 4973 - 4977
[19] Furukawa T., 2008, ANGEW CHEM, V120, P8171
[20] Catalytic Enantioselective Michael Addition of 1-Fluoro-bis(phenylsulfonyl)methane to α,β-Unsaturated Ketones Catalyzed by Cinchona Alkaloids
Furukawa, Tatsuya
Shibata, Norio
Mizuta, Satoshi
Nakamura, Shuichi
Toru, Takeshi
Shiro, Motoo
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8051 - 8054

← 1 2 3 4 5 6 7 →