ENANTIORETENTIVE ALKYLATION OF OXAZOLIDINONE ALUMINUM ENOLATES WITH EPOXIDES - PREPARATION OF UNCODED HOMOSERINE ANALOGS

被引:14
作者
SMITH, AB [1 ]
PASTERNAK, A [1 ]
YOKOYAMA, A [1 ]
HIRSCHMANN, R [1 ]
机构
[1] UNIV PENN,MONELL CHEM SENSES CTR,PHILADELPHIA,PA 19104
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(94)88404-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The alkylation of Karady/Seebach oxazolidinone enolates with epoxides, promoted by 2.1 equivalents of diethylaluminum chloride, furnishes ring-opened adducts in moderate-to-good yields with high diastereoselectivity. The method provides an effective approach to uncoded homoserine analogs and expands the utility of readily available oxazolidinones in asymmetric synthesis.
引用
收藏
页码:8977 / 8980
页数:4
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