Catalytic enantioselective Michael reaction of 1,3-dicarbonyl compounds via formation of chiral palladium enolate

被引：81

作者：

Hamashima, Y

Hotta, D

Umebayashi, N

Tsuchiya, Y

Suzuki, T

Sodeoka, M

机构：

[1] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Aoba Ku, Sendai, Miyagi 9808577, Japan

[2] Tohoku Pharmaceut Univ, Dept Synth Organ Chem, Aoba Ku, Sendai, Miyagi 9818558, Japan

[3] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 11-13期

关键词：

asymmetric catalysis; 1,3-dicarbonyl compounds; Michael reaction; palladium enolates; alpha; beta-unsaturated compounds;

D O I：

10.1002/adsc.200505199

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient catalytic enantioselective Michael reaction has been developed using chiral palladium complexes. Various substrates including beta-keto esters and 1,3-diketones reacted with alpha,beta-unsaturated carbonyl compounds to give the corresponding Michael adducts in good yield with up to 99% ee, thereby affording chiral quaternary carbon centers. In these reactions, chiral palladium enolates were generated as key intermediates, which acted cooperatively with a strong protic acid to activate the Michael acceptors for promotion of the C-C bond-forming reaction.

引用

页码：1576 / 1586

页数：11

共 118 条

[61] Hemilabile amidomonophosphine ligand-rhodium(I) complex-catalyzed asymmetric 1,4-addition of arylboronic acids to cycloalkenones [J].