Synthetic elaboration of the side chain of (R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine: A new regio- and stereoselective strategy to delta-functionalized beta-amino alcohols

被引：56

作者：

Reginato, G

Mordini, A

Caracciolo, M

机构：

[1] Dipto. di Chim. Organica U. Schiff, Centro CNR Composti Eterociclici, I-50121 Firenze

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 18期

关键词：

D O I：

10.1021/jo970619s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.

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页码：6187 / 6192

页数：6

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