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.

引用

页码：1965 / 1978

页数：14

共 37 条

[1] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS AND ALPHA-N-HYDROXYAMINO ACIDS VIA ELECTROPHILIC AMINATION OF BORNANESULTAM-DERIVED ENOLATES WITH 1-CHLORO-1-NITROSOCYCLOHEXANE
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 24 - ORGN
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BAMAUNG, N
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[7] ASYMMETRIC-SYNTHESIS OF THREO BETA-HYDROXY-ALPHA-N-METHYL AMINO-ACIDS AND MEBMT ANALOGS VIA EPOXIDES .1.
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[8] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS VIA CHIRAL IMINOLACTONE .2. PREPARATION AND ALKYLATION OF TRICYCLIC TEMPLATE DERIVED FROM PINENE AND MYRTENOL
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 25 - ORGN
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