Construction of chiral quaternary carbon centers by asymmetric alkylation of achiral lithium enolates mediated by chiral tetradentate ligands: Stoichiometric and catalytic approaches

被引：38

作者：

Yamashita, Y ^{[1
]}

Odashima, K ^{[1
]}

Koga, K ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 14期

关键词：

asymmetric synthesis; enantioselection; quaternization; catalysis;

D O I：

10.1016/S0040-4039(99)00299-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective asymmetric alkylation of achiral lithium enolates mediated by chiral tetradentate amine ligands is achieved to give chiral quaternary carbon centers. Turnover of a chiral tetradentate amine in the presence of an achiral bidentate amine during the reaction is also realized. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2803 / 2806

页数：4

共 21 条

[1] CATALYTIC ASYMMETRIC C-C BOND FORMATION - NEW ENOLATOLITHIUM AND ORGANOLITHIUM CHEMISTRY [J].

BERRISFORD, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (02) :178-180

[2]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

[3]

2-V

[4] ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS [J].

FUJI, K .

CHEMICAL REVIEWS, 1993, 93 (06) :2037-2066

[5] CONTROL OF DIASTEREOSELECTIVITY IN ALKYLATION OF CHIRAL LITHIUM ENOLATES MEDIATED BY A CHIRAL SECONDARY AMINE LIGAND [J].

HASEGAWA, Y ;

KAWASAKI, H ;

KOGA, K .

TETRAHEDRON LETTERS, 1993, 34 (12) :1963-1966

[6] CATALYTIC ASYMMETRIC BENZYLATION OF ACHIRAL LITHIUM ENOLATES USING A CHIRAL LIGAND FOR LITHIUM IN THE PRESENCE OF AN ACHIRAL LIGAND [J].

IMAI, M ;

HAGIHARA, A ;

KAWASAKI, H ;

MANABE, K ;

KOGA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8829-8830

[7]

JUARISTI E, 1993, SYNTHESIS-STUTTGART, P1271

[8] APPROACHES TO CATALYTIC ASYMMETRIC FORMATION AND REACTIONS LITHIUM ENOLATES [J].

KOGA, K ;

SHINDO, M .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1995, 53 (11) :1021-1032

[9] ASYMMETRIC-SYNTHESIS MEDIATED BY CHIRAL LIGANDS [J].

KOGA, K .

PURE AND APPLIED CHEMISTRY, 1994, 66 (07) :1487-1492

[10] METHODOLOGY FOR THE CONSTRUCTION OF QUATERNARY CARBON CENTERS [J].

MARTIN, SF .

TETRAHEDRON, 1980, 36 (04) :419-460

← 1 2 3 →