SHORT AND EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF CIS AND TRANS PYRROLIDINE-2,5-DICARBOXYLIC ACIDS

被引：28

作者：

EZQUERRA, J ^{[1
]}

RUBIO, A ^{[1
]}

PEDREGAL, C ^{[1
]}

SANZ, G ^{[1
]}

RODRIGUEZ, JH ^{[1
]}

RUANO, JLG ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,DEPT QUIM ORGAN,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 31期

关键词：

PYROGLUTAMATE; REGIOSELECTIVE REACTIONS; LITHIUM METHYL PARA-TOLYLSULFINYL ANION; 5-CARBOXY-L-PROLINE; 5-OXO-L-PIPECOLIC ACID; PUMMERER REACTION;

D O I：

10.1016/S0040-4039(00)74065-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-BOC-ethyl pyroglutamate 1 undergoes nucleophilic ring opening with lithium methyl p-tolyl sulfinyl anion delivering the p-tolylketosulfoxide 2.Treatment of 2 with TFA gave rise to a mixture of thioesters 3a,3b. The hydrolysis of 3b afforded the (2S, 5S) pirrolidine-2,5 dicarboxylic acid 5, a constituent of the red Alga Schizymenia dubyi. Under Pummerer reaction conditions (TFAA/Pyr), 2 yielded the 5-oxo-L-pipecolic acid derivative 6.

引用

页码：4989 / 4992

页数：4

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