Acid-base catalysis using chiral palladium complexes

被引：38

作者：

Sodeoka, M ^{[1
]}

Hamashima, Y

机构：

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

[2] RIKEN, Wako, Saitama 3510198, Japan

来源：

PURE AND APPLIED CHEMISTRY | 2006年 / 78卷 / 02期

关键词：

Bronsted acid; fluorination; Mannich reaction; Michael addition; palladium enolate; Bronsted base;

D O I：

10.1351/pac200678020477

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral Pd aqua and mu-hydroxo complexes were found to act as mild Bronsted acids and bases, and chiral Pd enolates were generated from these complexes even under acidic conditions. Highly enantioselective Michael addition, Mannich-type reaction, fluorination, and conjugate addition of amines have been developed based on the acid-base character of these Pd complexes.

引用

页码：477 / 494

页数：18

共 69 条

[1]

[Anonymous], COMPREHENSIVE ASYMME

[2]

[Anonymous], 2000, CATALYTIC ASYMMETRIC

[3] Enantioselective organocatalytic α-fluorination of aldehydes [J].

Beeson, TD ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828

[4] (α-monofluoroalkyl)phosphonates:: a class of isoacidic and "tunable" mimics of biological phosphates [J].

Berkowitz, DB ;

Bose, M .

JOURNAL OF FLUORINE CHEMISTRY, 2001, 112 (01) :13-33

[5] Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids [J].

Bernardi, L ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2005, (10) :1324-1326

[6] Enantioselective catalysis - Part 124. Enantioselective Michael reaction catalyzed by optically active transition metal complexes [J].

Brunner, H ;

Krumey, C .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 142 (01) :7-15

[7] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].

Christoffers, J ;

Baro, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690

[8]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

[9]

2-V

[10] The direct catalytic asymmetric Mannich reaction [J].

Córdova, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) :102-112

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