Asymmetric synthesis of ω-bromo-2(S)-azido acids as precursors for the synthesis of novel amino acids

被引：22

作者：

Lundquist, JT ^{[1
]}

Dix, TA ^{[1
]}

机构：

[1] Med Univ S Carolina, Dept Pharmaceut Sci, Charleston, SC 29425 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(97)10608-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of omega-bromo-2(S)-azido acids with side-chain lengths ranging from 3-5 methylene units has been synthesized. These intermediates enable the facile synthesis of chiral non-natural amino acids containing virtually any nucleophile capable of substituting the omega-bromo group. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：775 / 778

页数：4

共 7 条

[1]

*ACS, 1997, 214 ACS NAT M EXP PR, P97

[2] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030

[3] Asymmetric synthesis of non-natural homologues of lysine [J].

Kennedy, KJ ;

Lundquist, JT ;

Simandan, TL ;

Beeson, CC ;

Dix, TA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (14) :1937-1940

[4]

LUNDQUIST JT, UNPUB

[5]

MARCH J, 1985, ADV ORGANIC CHEM REA, P364

[6] UNCONVENTIONAL NUCLEOTIDE ANALOGUES .1. N9-PURINYL ALPHA-AMINO ACIDS [J].

NOLLET, AJH ;

HUTING, CM ;

PANDIT, UK .

TETRAHEDRON, 1969, 25 (24) :5971-&

[7]

SERVIGNE M, 1954, B SOC CHIM BIOL, V36, P1093

← 1 →