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

[1] ORGN 626-Organocatalytic enantioselective cyclopropanation of α,β-unsaturated aldehydes
Rios, Ramon
Sunden, Henrik
Vesely, Jan
Zhao, Gui-Ling
Diedzic, Pawel
Cordova, Armando
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
[2] 'On Water' Iminium/Enamine Catalysis: Organocatalytic Enantioselective Cyclopropanation of α,β-Unsaturated Aldehydes
Uria, Uxue
Vicario, Jose L.
Badia, Dolores
Carrillo, Luisa
Reyes, Efraim
Pesquera, Amaia
SYNTHESIS-STUTTGART, 2010, (04): : 701 - 713
[3] Organocatalytic enantioselective aziridination of α,β-unsaturated aldehydes
Vesely, Jan
Ibrahem, Ismail
Zhao, Gui-Ling
Rios, Ramon
Cordova, Armando
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (05) : 778 - 781
[4] Organocatalytic Enantioselective Aminosulfenylation of α,β-Unsaturated Aldehydes
Zhao, Gui-Ling
Rios, Ramon
Vesely, Jan
Eriksson, Lars
Cordova, Armando
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) : 8468 - 8472
[5] Enantioselective organocatalytic hydrophosphination of α,β-unsaturated aldehydes
Ibrahem, Ismail
Rios, Ramon
Vesely, Jan
Hammar, Peter
Eriksson, Lars
Himo, Fahmi
Cordova, Armando
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) : 4507 - 4510
[6] Organocatalytic asymmetric cyclopropanation of α,β-unsaturated aldehydes with arsonium ylides
Zhao, Yun-Hui
Zhao, Gang
Cao, Wei-Guo
TETRAHEDRON-ASYMMETRY, 2007, 18 (20) : 2462 - 2467
[7] Enantioselective organocatalytic Michael addition of isorhodanines to α,β-unsaturated aldehydes
Wu, Shanchao
Li, Yu
Zhang, Yongqiang
Fang, Kun
Dong, Guoqiang
Liu, Na
Miao, Zhenyuan
Yao, Jianzhong
Wang, Wei
Zhang, Wannian
Sheng, Chunquan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (16) : 3926 - 3933
[8] Enantioselective Organocatalytic Conjugate Addition of Fluorocarbon Nucleophiles to α,β-Unsaturated Aldehydes
Ullah, Farman
Zhao, Gui-Ling
Deiana, Luca
Zhu, Mingzhao
Dziedzic, Pawel
Ibrahem, Ismail
Hammar, Peter
Sun, Junliang
Cordova, Armando
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (39) : 10013 - 10017
[9] Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes
Li Hao
Ji YaFei
Li Jian
Zhang ShiLei
Yu ChenGuang
Wang Wei
SCIENCE CHINA-CHEMISTRY, 2010, 53 (01) : 135 - 139
[10] Enantioselective organocatalytic phospha-Michael reaction of α,β-unsaturated aldehydes
Luo, Xiaoyan
Zhou, Zhiqiang
Li, Xin
Liang, Xinmiao
Ye, Jinxing
RSC ADVANCES, 2011, 1 (04) : 698 - 705

← 1 2 3 4 5 →