A simple organocatalytic enantioselective cyclopropanation of α,β-unsaturated aldehydes

被引：167

作者：

Rios, Ramon ^{[1
]}

Sunden, Henrik ^{[1
]}

Vesely, Jan ^{[1
]}

Zhao, Gui-Ling ^{[1
]}

Dziedzic, Pawel ^{[1
]}

Cordova, Armando ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 07期

关键词：

asymmetric catalysis; cyclopropanes; domino reactions; halomalonates; organocatalysis; alpha; beta-unsaturated aldehydes;

D O I：

10.1002/adsc.200700032

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A highly chemo- and enantioselective organocatalytic cyclopropanation of alpha,beta-unsaturated aldehydes with bromomalonate and 2-bromoacetoacetate esters is presented. The reaction is catalyzed by chiral amines and gives access to 2-formylcyclopropanes in high yields and up to 99% ee.

引用

页码：1028 / 1032

页数：5

共 50 条

[31] Enantioselective Organocatalytic Aza-Michael Additions of Phthalimide Derivatives to α,β-Unsaturated Aldehydes
Ma, Shijun
Liu, Ming
Huang, Yaodong
Wang, Yongmei
CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (06) : 726 - 730
[32] Development of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with α,β-unsaturated aldehydes
Borths, Christopher J.
Carrera, Diane E.
MacMillan, David W. C.
TETRAHEDRON, 2009, 65 (33) : 6746 - 6753
[33] Organocatalytic Enantioselective Aziridination of α-Substituted α,β-Unsaturated Aldehydes: Asymmetric Synthesis of Terminal Aziridines
Deiana, Luca
Zhao, Gui-Ling
Lin, Shuangzheng
Dziedzic, Pawel
Zhang, Qiong
Leijonmarck, Hans
Cordova, Armando
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3201 - 3207
[34] Organocatalytic enantioselective [3+2]cycloaddition of azomethine ylides and α,β-unsaturated aldehydes
Vicario, Jose L.
Reboredo, Silvia
Badia, Dolores
Carrillo, Luisa
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) : 5168 - 5170
[35] Organocatalytic γ-oxidation of α,β-unsaturated aldehydes
Chrominski, Mikolaj
Giedyk, Maciej
Gryko, Dorota
ARKIVOC, 2014, : 135 - 145
[36] Organocatalytic Enantioselective Continuous-Flow Cyclopropanation
Llanes, Patricia
Rodriguez-Escrich, Carles
Sayalero, Sonia
Pericas, Miquel A.
ORGANIC LETTERS, 2016, 18 (24) : 6292 - 6295
[37] Enantioselective organocatalytic cyclopropanation via ammonium ylides
Papageorgiou, CD
de Dios, MAC
Ley, SV
Gaunt, MJ
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (35) : 4641 - 4644
[38] Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media
Ghosh, Subrata K.
Dhungana, Kritanjali
Headley, Allan D.
Ni, Bukuo
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (41) : 8322 - 8325
[39] Enantioselective organocatalytic Mukaiyama-Michael addition of silyl enol ethers to α,β-unsaturated aldehydes
Wang, W
Li, H
Wang, J
ORGANIC LETTERS, 2005, 7 (08) : 1637 - 1639
[40] Direct and enantioselective organocatalytic α-chlorination of aldehydes
Brochu, MP
Brown, SP
MacMillan, DWC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) : 4108 - 4109

← 1 2 3 4 5 →