CuI-Catalyzed conjugate addition of ethyl propiolate

被引：53

作者：

Fujimori, Shinji ^{[1
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] ETH, Lab Organ Chem, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 26期

基金：

澳大利亚研究理事会;

关键词：

alkynes; asymmetric synthesis; copper; nucleophilic addition; synthetic methods;

D O I：

10.1002/anie.200701098

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) More functionality possible: The conjugate addition of ethyl propiolate to Meldrum's acid derived acceptors is described. These reactions proceed under mild conditions employing substoichiometric amounts of a copper(I) species generated in situ. When chiral acceptors are employed as substrates, the additions are stereoselective and provide the addition adduct with high diastereoselectivity. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4964 / 4967

页数：4

共 54 条

[1]

Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221

[2] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].

Anand, NK ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688

[3] Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group [J].

Aschwanden, Patrick ;

Stephenson, Corey R. J. ;

Carreira, Erick M. .

ORGANIC LETTERS, 2006, 8 (11) :2437-2440

[4]

Aschwanden P, 2005, ACETYLENE CHEMISTRY: CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE, P101

[5] Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions [J].

Boyall, D ;

Frantz, DE ;

Carreira, EM .

ORGANIC LETTERS, 2002, 4 (15) :2605-2606

[6] Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes [J].

Boyall, D ;

López, F ;

Sasaki, H ;

Frantz, D ;

Carreira, EM .

ORGANIC LETTERS, 2000, 2 (26) :4233-4236

[7]

Breit B, 2002, MODERN ORGANOCOPPER CHEMISTRY, P188, DOI 10.1002/3527600086.ch6

[8]

BRUHN M, 1976, TETRAHEDRON LETT, V17, P235

[9] Gold(I)-catalyzed formation of 4-alkylidene-1,3-dioxolan-2-ones from propargylic tert-butyl carbonates [J].

Buzas, A ;

Gagosz, F .

ORGANIC LETTERS, 2006, 8 (03) :515-518

[10] The first palladium-catalyzed 1,4-addition of terminal alkynes to conjugated enones [J].

Chen, L ;

Li, CJ .

CHEMICAL COMMUNICATIONS, 2004, (20) :2362-2364

← 1 2 3 4 5 6 →