Allenylzincs and tert-butylsulfinylimines: a fruitful marriage for synthesis

被引：16
作者：
Botuha, Candice
Chemla, Fabrice [1 ]
Ferreira, Franck
Louvel, Julien
Perez-Luna, Alejandro
机构：
[1] Univ Paris 06, F-75005 Paris, France
来源：
TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 9-10期
关键词：
CHIRAL ORGANOLITHIUM COMPOUNDS; ASYMMETRIC-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESES; ENANTIOSELECTIVE SYNTHESIS; CONFIGURATIONAL STABILITY; RACEMIC ALLENYLZINC; COMMON INTERMEDIATE; KINETIC RESOLUTION; CONCISE SYNTHESIS; NATURAL-PRODUCTS;
D O I：
10.1016/j.tetasy.2010.04.044
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The stereoselective synthesis of alkynyl 1,2-amino alcohols by the addition of 3-chloro- and 3-methoxy-methoxy- allenylzincs to chiral tert-butylsulfinylimines is described. The methodology is applicable to the preparation of alkynyl 2-amino-1,3-diols (O,N,O stereotriads) using alpha-alkoxy tert-butylsulfinylimines as chiral starting materials. The scope and limitations of the methodology along with recent applications to the efficient asymmetric syntheses of natural and/or bioactive alkaloids and polyhydroxylated alkaloids are presented. (C) 2010 Elsevier Ltd. All rights reserved.
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页码：1147 / 1153
页数：7
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