Scope and limitations in the use of N-(PhF)serine-derived cyclic sulfamidates for amino acid synthesis

被引：52

作者：

Wei, L ^{[1
]}

Lubell, WD ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2001年 / 79卷 / 01期

关键词：

glutamate; amino acid; cyclic sulfamidate; proline;

D O I：

10.1139/cjc-79-1-94

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ring-opening of N-(PhF)serine-derived cyclic sulfamidate 17 was achieved with different nucleophiles (beta -keto esters, beta-keto ketones, dimethyl malonate, nitroethane, sodium azide, imidazole, and potassium thiocyanate) to prepare a variety of amino acid analogs. Two different pathways for ring opening of 17 were elucidated: direct nucleophilic displacement, as well as beta -elimination followed by Michael addition. Furthermore, beta -keto ester and beta -keto ketone products 18k,18m, and 18i were converted to prolines and pyrazole amino acids.

引用

页码：94 / 104

页数：11

共 35 条

[31] ENANTIOMERICALLY PURE DIMETHYL (2S)-N-(9-PHENYLFLUOREN-9-YL)-3,4-DIDEHYDROGLUTAMATE AS CHIRAL EDUCT - CHIROSPECIFIC SYNTHESIS OF (+)-5-O-CARBAMOYLPOLYOXAMIC ACID AND 3-ALKYLGLUTAMATES [J].