ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS AND ALPHA-N-HYDROXYAMINO ACIDS FROM N-ACYLBORNANE-10,2-SULTAMS - 1-CHLORO-1-NITROSOCYCLOHEXANE AS A PRACTICAL [NH2+] EQUIVALENT

被引：94
作者：
OPPOLZER, W
TAMURA, O
DEERBERG, J
机构：
[1] Départment de Chimie Organique, Université de Genève, Genève
来源：
HELVETICA CHIMICA ACTA | 1992年 / 75卷 / 06期
关键词：
D O I：
10.1002/hlca.19920750622
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Successive treatment of N-acylsultams 3 with sodium hexamethyldisilazide, 1-chloro-1-nitrosocyclohexane (1), and aq. HCl gave diastereoisomerically pure, crystalline N-hydroxyamino-acid derivatives 5. These were converted into various amino acids 7, N-hydroxyamino acids 8, and an N-Boc-amino acid 9. (S,S)-Isoleucine (17) and (SS)-2-acetamido-3-phenylbutyric acid (23) were obtained from N-crotonoylsultam 15 via 1,4-addition of an organomagnesium or organocopper reagent followed by enolate 'amination' with 1.
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页码：1965 / 1978
页数：14
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