ON THE 1,3-ISOMERIZATION OF NONRACEMIC ALPHA-(ALKOXY)ALLYL STANNANES

被引：94

作者：

MARSHALL, JA

WELMAKER, GS

GUNG, BW

机构：

[1] Department of Chemistry, The University of South Carolina, Columbia

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 02期

关键词：

D O I：

10.1021/ja00002a038

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A set of optically active (E)-alpha-(alkoxy)allyl stannanes 10-13 and ent-10-13 was prepared by reduction of the acyl stannanes 4-6 with (R)-(+)-BINAL-H or LiAlH4-Chirald and protection of the resulting hydroxy stannanes with MOMCl or BOMCl. On treatment with BF3.OEt2 these stannanes rearranged stereospecifically to the (Z)-gamma-(alkoxy)allyl stannanes 21-24 by 1,3-migration of Bu3Sn. The rearrangement was shown to take place by an intermolecular anti pathway. Addition of the gamma-alkoxy stannanes 21-24 to representative aldehydes afforded optically active syn-1,2-diol monoethers 25-28 as the major diastereomers with high anti S(E)' stereoselectivity.

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页码：647 / 656

页数：10

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