Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis

被引：86
|
作者：
Chippindale, AM
Davies, SG
Iwamoto, K
Parkin, RM
Smethurst, CAP
Smith, AD
Rodriguez-Solla, H
机构：
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Univ Oxford, Chem Crystallog Lab, Oxford OX1 3PD, England
来源：
TETRAHEDRON | 2003年 / 59卷 / 18期
关键词：
lithium amide; conjugate addition; ring closing metathesis;
D O I：
10.1016/S0040-4020(03)00411-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diastereoselective conjugate addition of lithium (S)-N-allyl-N-alpha-methylbenzylamide to a range of alpha,beta-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic beta-amino esters in high d.e. Alternatively, conjugate addition to alpha,beta-unsaturated Weinreb amides, functional group conversion and ring closing metathesis affords cyclic amines in high d.e. The further application of this methodology to the synthesis of a range of carbocyclic beta-amino esters via conjugate addition, enolate alkylation and ring closing metathesis is also described. Application of this methodology affords, after deprotection, (S)-homoproline, (S)-homopipecolic acid, (S)-coniine and (1S,2S)-trans-pentacin. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3253 / 3265
页数：13
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