Highly enantioselective synthesis of chiral imides and derived products via chiral base desymmetrisation

被引：41

作者：

Adams, DJ ^{[1
]}

Blake, AJ ^{[1
]}

Cooke, PA ^{[1
]}

Gill, CD ^{[1
]}

Simpkins, NS ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

TETRAHEDRON | 2002年 / 58卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

asymmetric synthesis; chiral lithium amide; imides;

D O I：

10.1016/S0040-4020(02)00367-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective deprotonation of several ring-fused imides with a chiral base, followed by electrophilic quenching, gives a range of chiral products in good yield and in greater than or equal to91% ee. The absolute stereochemistry of two of the products was determined by X-ray crystallography. A number of the imide products were subjected to further, highly regioselective, transformations, including enolate substitution, reduction and thionation. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：4603 / 4615

页数：13

共 25 条

[1] New symmetry-breaking deprotonation reactions of cyclic imides using a chiral lithium amide base [J].

Adams, DJ ;

Simpkins, NS ;

Smith, TJN .

CHEMICAL COMMUNICATIONS, 1998, (15) :1605-1606

[2] The asymmetric synthesis of phosphorus- and sulfur-containing tricarbonyl(η6-arene)chromium complexes using the chiral base approach [J].

Ariffin, A ;

Blake, AJ ;

Ewin, RA ;

Li, WS ;

Simpkins, NS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (21) :3177-3189

[3] FORMATION OF FUSED TRICYCLIC AZETIDINONES AND PYRROLIDINONES BY INTRAMOLECULAR SH2 PROCESSES [J].

BECKWITH, ALJ ;

BOATE, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4339-4348

[4] The enantioselective generation of bridgehead enolates [J].

Blake, AJ ;

Giblin, GMP ;

Kirk, DT ;

Simpkins, NS ;

Wilson, C .

CHEMICAL COMMUNICATIONS, 2001, (24) :2668-2669

[5] Enantioselective synthesis of phospholanes using chiral lithium amide desymmetrisation [J].

Blake, AJ ;

Hume, SC ;

Li, WS ;

Simpkins, NS .

TETRAHEDRON, 2002, 58 (23) :4589-4602

[6] Concerning the synthesis and enantioselective rearrangements of episulfoxides [J].

Blake, AJ ;

Cooke, PA ;

Kendall, JD ;

Simpkins, NS ;

Westaway, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (02) :153-163

[7] THE ALPHA-BROMOESTER-IMINE CONDENSATION PROMOTED BY ZINC-TRIMETHYLCHLOROSILANE - A STEREOSPECIFIC SHORT FORMAL SYNTHESIS OF (+/-)-CARBAPENEM ANTIBIOTICS AND RELATED-COMPOUNDS [J].

COSSIO, FP ;

ODRIOZOLA, JM ;

OIARBIDE, M ;

PALOMO, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (02) :74-76

[8] ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES [J].

COX, PJ ;

SIMPKINS, NS .

TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :1-26

[9]

de Koning H, 1998, EUR J ORG CHEM, V1998, P1729

[10] Chiral base route to cyclic polyols: asymmetric synthesis of aminodeoxyconduritols and conduritol F [J].

de Sousa, SE ;

O'Brien, P ;

Pilgram, CD .

TETRAHEDRON LETTERS, 2001, 42 (45) :8081-8083

← 1 2 3 →