Asymmetric conjugate addition to α-halo enones:: Dramatic effect of styrene on the enantioselectivity

被引：49

作者：

Li, Kangying ^{[1
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 45期

关键词：

asymmetric synthesis; conjugate addition; copper; homogeneous catalysis; radicals;

D O I：

10.1002/anie.200602417

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple trick could prove generally valuable for asymmetric copper-catalyzed conjugate addition reactions. It was found that the enantioselectivities of such reactions of dialkyl zinc reagents with α-halo enones in the presence of chiral phosphorimidite ligands were dramatically improved upon the addition of styrene, which acts as a radical scavenger to suppress the competitive non-asymmetric radical pathway (see example). (Chemical Equation Presented) © 2006 Wiley-VCH Verlag GmbH &. Co. KGaA.

引用

页码：7600 / 7603

页数：4

共 50 条

[21] Chiral monodentate phosphine ligand MOP for transition metal-catalyzed asymmetric reactions [J].

Hayashi, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :354-362

[22] A NEW ALPHA-IODINATION OF KETONES USING IODINE-CERIUM(IV) AMMONIUM-NITRATE [J].

HORIUCHI, CA ;

KIJI, S .

CHEMISTRY LETTERS, 1988, (01) :31-34

[23] USE OF LITHIUM ORGANOCUPRATE ADDITIONS AS MODELS FOR AN ELECTRON-TRANSFER PROCESS [J].

HOUSE, HO .

ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (02) :59-67

[24] Copper-carbene catalysts - Copper carbene complexes: Advanced catalysts, new insights [J].

Kirmse, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (10) :1088-1093

[25]

Kirmse W, 2003, ANGEW CHEM, V115, P1120

[26] CONSEQUENCES OF BETA-BROMO SUBSTITUTION ON THE COURSE OF ALLYLMETAL ADDITIONS TO 1-OXASPIRO[4.5]DEC-7-EN-6-ONE [J].

KLEMEYER, HJ ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7924-7927

[27]

Knochel P., 2001, ORG REACTIONS, V58, P417

[28] One-pot synthesis of 2-aminothiazoles using supported reagents [J].

Kodomari, M ;

Aoyama, T ;

Suzuki, Y .

TETRAHEDRON LETTERS, 2002, 43 (09) :1717-1720

[29] ALPHA-KETO DIANION PRECURSORS VIA CONJUGATE ADDITIONS TO CYCLIC ALPHA-BROMO ENONES [J].

KOWALSKI, CJ ;

WEBER, AE ;

FIELDS, KW .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) :5088-5093

[30]

KRAUSE N, 2001, MDOERN ORGANOCOPPER

← 1 2 3 4 5 →