Grignard reactions of 4-substituted-2-keto-1,3-dioxanes: Highly diastereoselective additions controlled by a remote alkyl group

被引：13

作者：

Bailey, WF ^{[1
]}

Reed, DP ^{[1
]}

Clark, DR ^{[1
]}

Kapur, GN ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 12期

关键词：

D O I：

10.1021/ol015914k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The reactions of Grignard reagents with a representative series of simple cis-2-keto-4-substituted-1,3-dioxanes have been investigated. The stereochemical outcome of these highly diastereoselective additions (dr > 90:10) is consonant with Cram's chelate model on the assumption that RMgX coordinates preferentially with the ring oxygen remote from the C(4) substituent.

引用

页码：1865 / 1868

页数：4

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