Use of (S)-N-tert-butoxycarbonylaziridine-2-carboxylate derivatives for alpha-amino acid synthesis

被引：67

作者：

Baldwin, JE ^{[1
]}

Farthing, CN ^{[1
]}

Russell, AT ^{[1
]}

Schofield, CJ ^{[1
]}

Spivey, AC ^{[1
]}

机构：

[1] OXFORD CTR MOLEC SCI, OXFORD OX1 3QY, ENGLAND

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 21期

关键词：

D O I：

10.1016/0040-4039(96)00676-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S)tert-Butyl-N-tert-butoxycarbonylaziridine-2-carboxylate and (S)-tert-butyl-N-tert-butoxycarbonylaziridine-2-carboxamide were synthesised and found to react with copper 'catalysed' Grignard reagents to give protected alpha-amino acids in moderate to good yields. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：3761 / 3764

页数：4

相关论文

共 22 条

[1] SYNTHESIS OF OPTICALLY PURE ALPHA-AMINO-ACIDS VIA SALTS OF ALPHA-AMINO-BETA-PROPIOLACTONE [J].

ARNOLD, LD ;

MAY, RG ;

VEDERAS, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2237-2241

[2] NUCLEOPHILIC RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH WITTIG REAGENTS - AN ENANTIOEFFICIENT SYNTHESIS OF UNSATURATED AMINO-ACIDS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ROBINSON, NG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :153-155

[3] AMINO-ACID SYNTHESIS VIA RING-OPENING OF N-SULFONYL AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS [J].

BALDWIN, JE ;

SPIVEY, AC ;

SCHOFIELD, CJ ;

SWEENEY, JB .

TETRAHEDRON, 1993, 49 (28) :6309-6330

[4] THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ONEIL, IA ;

SCHOFIELD, C ;

SPIVEY, AC ;

SWEENEY, JB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1852-1854

[5]

BALGOWICZ JA, 1985, TETRAHEDRON, V41, P1833

[6] N,N-DIMETHYLFORMAMIDE DINEOPENTYLACETAL - REAGENT FOR ESTERIFYING CARBOXYLIC ACIDS WITH BENZYL ALCOHOLS [J].

BUCHI, H ;

ESCHENMOSER, A ;

STEEN, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1964, 3 (01) :62-&

[7]

CHANG BC, 1971, J AM CHEM SOC, V93, P4004

[8] FACILE SYNTHESIS OF TERT-BUTYL ESTER OF N-PROTECTED AMINO-ACIDS WITH TERT-BUTYL BROMIDE [J].

CHEVALLET, P ;

GARROUSTE, P ;

MALAWSKA, B ;

MARTINEZ, J .

TETRAHEDRON LETTERS, 1993, 34 (46) :7409-7412

[9] SYNTHESIS OF ALPHA-AMINO-ACIDS BY RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH CARBON NUCLEOPHILES [J].

CHURCH, NJ ;

YOUNG, DW .

TETRAHEDRON LETTERS, 1995, 36 (01) :151-154

[10] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&