First enantioselective organocatalytic conjugate addition of aldehydes to vinyl phosphonates

被引：91

作者：

Sulzer-Mosse, Sarah ^{[1
]}

Tissot, Matthieu ^{[1
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva, Switzerland

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 19期

关键词：

D O I：

10.1021/ol7015498

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral amines catalyze the enantioselective conjugate addition of aldehydes to vinyl phosphonates in high yields and with enantioselectivities up to 97% ee. This novel process provides synthetically useful chiral gamma-geminal phosphonate aldehydes which can be easily converted in a few steps into chiral beta-substituted vinyl phosphonates with conservation of the optical purity.

引用

页码：3749 / 3752

页数：4

共 50 条

[41] Enantioselective organocatalytic α-fluorination of aldehydes
Beeson, TD
MacMillan, DWC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) : 8826 - 8828
[42] Organocatalytic enantioselective hydrophosphonylation of aldehydes
Alegre-Requena, Juan V.
Marques-Lopez, Eugenia
Sanz Miguel, Pablo J.
Herrera, Raquel P.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (08) : 1258 - 1264
[43] Formal highly enantioselective organocatalytic addition of fluoromethyl anion to α,β-unsaturated aldehydes
Alba, Andrea-Nekane
Companyo, Xavier
Moyano, Albert
Rios, Ramon
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[44] Organocatalytic enantioselective conjugate addition-cyclization domino reactions of o-N-protected aminophenyl α,β-unsaturated aldehydes
Heo, Seungpyeong
Kim, Shinae
Kim, Sung-Gon
TETRAHEDRON LETTERS, 2013, 54 (36) : 4978 - 4981
[45] Highly enantioselective organocatalytic conjugate addition of nitromethane to α,β-unsaturated aldehydes:: Three-step synthesis of optically active baclofen
Zu, Liansuo
Xie, Hexin
Li, Hao
Wang, Han
Wang, Wei
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) : 2660 - 2664
[46] Enantioselective organocatalytic α-vinylation of aldehydes
Skucas, Eduardas
MacMillan, David W. C.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[47] Enantioselective organocatalytic α-fluorination of aldehydes
MacMillan, D.W.C. (Dmacmill@caltech.edu), 1600, American Chemical Society (127):
[48] Organocatalytic Enantioselective α-Alkylation of Aldehydes
Vesely, Jan
Rios, Ramon
CHEMCATCHEM, 2012, 4 (07) : 942 - 953
[49] Enantioselective organocatalytic α-arylation of aldehydes
Allen, Anna E.
MacMillan, David W. C.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
[50] Diastereo- and Enantioselective Organocatalytic Direct Conjugate Addition of γ-Butenolide to Chalcones
Zhang, Yinan
Yu, Chenguang
Ji, Yafei
Wang, Wei
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (06) : 1303 - 1306

← 1 2 3 4 5 →