Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides

被引：13
|
作者：
West, Thomas H. [1 ]
Spoehrle, Stephanie S. M. [1 ]
Smith, Andrew D. [1 ]
机构：
[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
来源：
TETRAHEDRON | 2017年 / 73卷 / 29期
关键词：
23]-rearrangement; Isothiourea catalysis; Allylic ammonium ylides; Enantioselective catalysis; alpha-amino esters; AMINO-ACID DERIVATIVES; C(SP(3))-H ARYLATION; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; BENZOTETRAMISOLE; GENERATION; AMINATION;
D O I：
10.1016/j.tet.2017.01.062
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangement of N,N-diallyl allylic ammonium ylides is explored as a key part of a route to free functionalised alpha-amino esters and piperidines. The [2,3]-sigmatropic rearrangement proceeds with excellent diastereo- and enantiocontrol (>95:5 dr; up to 97% ee), with the resultant N,N-diallyl alpha-amino esters undergoing either mono- or bis-Nallyl deprotection. Bis-N-allyl deprotection leads to free alpha-amino esters, while the mono-deprotection strategy has been utilized in the synthesis of a target functionalised piperidine. (C) 2017 Published by Elsevier Ltd.
引用
收藏
页码：4138 / 4149
页数：12
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