New symmetry-breaking deprotonation reactions of cyclic imides using a chiral lithium amide base

被引：16

作者：

Adams, DJ ^{[1
]}

Simpkins, NS ^{[1
]}

Smith, TJN ^{[1
]}

机构：

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

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 15期

关键词：

D O I：

10.1039/a803574a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of various N-substituted succinimides, possessing additional three-, four- or five-membered ring-fusion, with a mixture of chiral lithium amide base and Me3SiCl, enables enantioselective silylation to give products in up to 95% ee.

引用

页码：1605 / 1606

页数：2

共 17 条

[1] FORMATION OF FUSED TRICYCLIC AZETIDINONES AND PYRROLIDINONES BY INTRAMOLECULAR SH2 PROCESSES
BECKWITH, ALJ
BOATE, DR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) : 4339 - 4348
[2] Blake AJ, 1997, SYNLETT, P919
[3] THE EFFECT OF ADDED SALTS ON ENANTIOSELECTIVE TRANSFORMATIONS OF CYCLIC-KETONES BY CHIRAL LITHIUM AMIDE BASES
BUNN, BJ
SIMPKINS, NS
SPAVOLD, Z
CRIMMIN, MJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (24): : 3113 - 3116
[4] ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES
COX, PJ
SIMPKINS, NS
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (01) : 1 - 26
[5] Episulfone substitution and ring-opening reactions via alpha-sulfonyl carbanion intermediates
Dishington, AP
Douthwaite, RE
Mortlock, A
Muccioli, AB
Simpkins, NS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (03): : 323 - 337
[6] Chiral base mediated asymmetric synthesis of tricarbonyl(eta(6)-arene)-chromium complexes
Ewin, RA
MacLeod, AM
Price, DA
Simpkins, NS
Watt, AP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 401 - 415
[7] Asymmetric synthesis of epibatidine by use of a novel enantioselective sulfinate elimination reaction
Jones, CD
Simpkins, NS
Giblin, GMP
[J]. TETRAHEDRON LETTERS, 1998, 39 (09) : 1023 - 1024
[8] ASYMMETRIC-SYNTHESIS MEDIATED BY CHIRAL LIGANDS
KOGA, K
[J]. PURE AND APPLIED CHEMISTRY, 1994, 66 (07) : 1487 - 1492
[9] Rate of deprotonation of a simple ketone by lithium diisopropylamide
Majewski, M
Nowak, P
[J]. TETRAHEDRON LETTERS, 1998, 39 (13) : 1661 - 1664
[10] Milewska MJ, 1997, J ORG CHEM, V62, P1860

← 1 2 →