Stereoselective reactions. Part 31: Catalytic asymmetric alkylation of achiral lithium enolates using a chiral tetradentate amine in the presence of an achiral bidentate amine

被引：27

作者：

Imai, M ^{[1
]}

Hagihara, A ^{[1
]}

Kawasaki, H ^{[1
]}

Manabe, K ^{[1
]}

Koga, K ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2000年 / 56卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(99)00995-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric alkylation of achiral lithium enolates of 1-tetralone and cyclohexanone with reactive alkyl halides was realized by using a combination of a chiral tetradentate amine (similar to 0.05 equiv.) and an achiral bidentate amine (2 equiv.). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：179 / 185

页数：7

共 21 条

[1]

BACHMANN WE, 1949, J AM CHEM SOC, V71, P3467

[2]

Caine D., 1991, COMPREHENSIVE ORGANI, V3

[3]

CAREY FA, 1990, ADV ORGANIC CHEM B, pCH1

[4] 1,1,4,7,10,10-hexamethyltriethylenetetramine: a reagent to enhance the rate of alkylation reaction of the lithium enolate of 1-tetralone with alkyl halides [J].

Goto, M ;

Akimoto, K ;

Aoki, K ;

Shindo, M ;

Koga, K .

TETRAHEDRON LETTERS, 1999, 40 (46) :8129-8132

[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] Enantioselective alkylation of lactams and lactones via lithium enolate formation using a chiral tetradentate lithium amide in the presence of lithium bromide [J].

Matsuo, J ;

Kobayashi, S ;

Koga, K .

TETRAHEDRON LETTERS, 1998, 39 (52) :9723-9726

[9]

MEKELBURGER HB, 1991, COMPREHENSIVE ORGANI, V3

[10] ENANTIOSELECTIVE ALKYLATION OF KETONES VIA CHIRAL, NON-RACEMIC LITHIOENAMINES - AN ASYMMETRIC-SYNTHESIS OF ALPHA-ALKYL AND ALPHA, ALPHA'-DIALKYL CYCLIC-KETONES [J].

MEYERS, AI ;

WILLIAMS, DR ;

ERICKSON, GW ;

WHITE, S ;

DRUELINGER, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3081-3087

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