ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS AND ALPHA-N-HYDROXYAMINO ACIDS VIA ELECTROPHILIC AMINATION OF BORNANESULTAM-DERIVED ENOLATES WITH 1-CHLORO-1-NITROSOCYCLOHEXANE

被引：123

作者：

OPPOLZER, W

TAMURA, O

机构：

[1] Département de Chimie Organique, Université de Genéve

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(00)94411-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Successive treatment of N-acylsultams 3 with NaN(TMS)2, l-chloro-1-nitrosocyclohexane (1) and 1N aq. HCl gave diastereomerically pure, crystalline Nhydroxyamino acid derivatives 4. Products 4 were converted to various amino acids 6, an NBOC-amino acid 8 and to N-hydroxyamino acids 9. (S,S)-Isoleucine (16) was obtained from N-crotonoylsultam 13 via an organomagnesium- 1,4-addition/enolate trapping process generating two stereogenic centers. © 1990.

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页码：991 / 994

页数：4

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