Enantioselective synthesis of cis-(2S,3R)- and trans-(2S,3S)-piperidinedicarboxylic acids using domino: allylic acetate and Ireland-Claisen rearrangements and Michael addition as the key steps

被引：14
作者：
Garrido, Narciso M. [1 ]
Rosa Sanchez, M. [1 ]
Diez, David [1 ]
Sanz, Francisca [2 ]
Urones, Julio G. [1 ]
机构：
[1] Univ Salamanca, Dept Quim Organ, E-37008 Salamanca, Spain
[2] Univ Salamanca, Serv Rayos X, Fac Ciencias Quim, E-37008 Salamanca, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 08期
关键词：
BAYLIS-HILLMAN REACTION; BETA-AMINO ACIDS; ASYMMETRIC-SYNTHESIS; DICARBOXYLIC-ACIDS; DERIVATIVES; ANALOGS; CIS;
D O I：
10.1016/j.tetasy.2011.04.015
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An enantioselective synthesis of (2S,3R)-piperidine-2,3-dicarboxylic acid and (2S,3.9-piperidine-2,3-dicarboxylic acid is described. This synthesis was mainly based on a delta-amino acid formation via a domino reaction: allylic acetate rearrangement, stereoselective Ireland-Claisen rearrangement and asymmetric Michael addition protocol from a Baylis-Hillman adduct, in which the cinnamaldehyde double bond is a masked carboxylic functionality, and a cerium(IV) ammonium nitrate promoted monodebenzylation. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：872 / 880
页数：9
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