Experimental and Computational Studies of the Diastereoselective Alkylations of 3-Substituted γ-Sultams

被引：4

作者：

Fauber, Benjamin P. ^{[1
]}

Clagg, Kyle ^{[1
]}

Gibbons, Paul ^{[1
]}

Rene, Olivier ^{[1
]}

机构：

[1] Genentech Inc, Discovery Chem, San Francisco, CA 94080 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 01期

关键词：

ALPHA-SULFONYL CARBANIONS; RAY CRYSTAL-STRUCTURE; ELECTROPHILIC SUBSTITUTION; SATURATED CARBON; LITHIUM-SALTS; AB-INITIO; STEREOCHEMISTRY; 1,3-DITHIANES; SULFONAMIDES; REACTIVITY;

D O I：

10.1021/jo502506j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report that chiral 3-substituted gamma-sultam alpha-carbanions undergo diastereoselective alkylation reactions with alkyl halides to predominantly produce trans-3,5-disubstituted gamma-sultam products. Quantum mechanical calculations provided a stereoelectronic rationale for the observed diastereoselectivity.

引用

页码：685 / 689

页数：5

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