ALKYLATIONS OF CHIRAL, PHOSPHORYL-STABILIZED AND THIOPHOSPHORYL-STABILIZED CARBANIONS

被引：49

作者：

DENMARK, SE

CHEN, CT

机构：

[1] Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 48期

关键词：

D O I：

10.1021/ja00153a009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general method for the preparation of enantiomerically enriched phosphonic acids and phosphonates with three different a-substitution patterns (aryl, alkyl, and alkoxy) has been developed. Anions derived from enantiomerically enriched thiophosphonamidates (2-thioxo-1,3,2-oxazaphosphorinanes) underwent smooth electrophilic substitutions with excellent diastereoselectivity for both cis and trans stereoisomers. Highly enantioselective synthesis of alpha-alkoxyphosphonates in either antipodal form can be achieved by the employment of highly diastereoselective alkylation with anions derived from the corresponding P-methoxymethyl analogs in the presence of HMPA or PMDTA. Implications for the aggregation states and reactive conformations of the anions are discussed.

引用

页码：11879 / 11897

页数：19

共 188 条

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