HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF THREO OR ERYTHRO AMINOALKYL EPOXIDES FROM ALPHA-AMINO-ACIDS

被引：105

作者：

BARLUENGA, J ^{[1
]}

BARAGANA, B ^{[1
]}

CONCELLON, JM ^{[1
]}

机构：

[1] UNIV OVIEDO,CSIC,INST QUIM ORGANOMETAL ENRIQUE MOLES,E-33071 OVIEDO,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 21期

关键词：

D O I：

10.1021/jo00126a019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Chloro-alpha'-(dibenzylamino) methylketones 3 are synthesized in enantiomerically pure form starting from alpha-amino acids. Reduction of amino ketones 3 and further epoxidation affords three aminoalkyl epoxides 6 with diastereoisomeric excess ranging between 94% and 98%. The synthesis of erythro amino epoxides 9 is also described by reaction of alpha-amino aldehydes 7 with in situ generated (halomethyl)lithium. Amino epoxides 9 were obtained with a diastereoisomeric excess ranging between 91% and 98%.

引用

页码：6696 / 6699

页数：4

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