HIGHLY DIASTEREOSELECTIVE SE' ADDITIONS OF ENANTIOENRICHED ALLENYLSTANNANES TO (S)-2-(BENZYLOXY)PROPANAL

被引：65

作者：

MARSHALL, JA

WANG, XJ

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 10期

关键词：

D O I：

10.1021/jo00010a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The BF3-promoted addition of (S)-allenylstannane (S)-6 to aldehyde 16 afforded a 68:32 mixture of diastereomeric homopropargylic alcohols 17 and 18 whereas MgBr2-promoted addition gave adduct 17 as the exclusive product. The (R)-allenylstannane (R)-6, on the other hand, yielded a 30:1 mixture of syn and anti alcohol adducts 19 and 20 with BF3.OEt2 and a 1:92 mixture favoring the anti adduct 20 under MgBr2 catalysis.

引用

页码：3211 / 3213

页数：3

共 20 条

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