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

Authors
EZQUERRA J RUBIO A PEDREGAL C SANZ G RODRIGUEZ JH RUANO JLG
Citation
J. Ezquerra et al., SHORT AND EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF CIS AND TRANS PYRROLIDINE-2,5-DICARBOXYLIC ACIDS, Tetrahedron letters, 34(31), 1993, pp. 4989-4992
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
31
Year of publication
1993
Pages
4989 - 4992
Database
ISI
SICI code
0040-4039(1993)34:31<4989:SAEESO>2.0.ZU;2-T
Abstract
N-BOC-ethyl pyroglutamate 1 undergoes nucleophilic ring opening with l ithium methyl p-tolyl sulfinyl anion delivering the p-tolylketosulfoxi de 2.Treatment of 2 with TFA gave rise to a mixture of thioesters 3a,3 b. The hydrolysis of 3b afforded the (2S, 5S) pirrolidine-2,5 dicarbox ylic acid 5, a constituent of the red Alga Schizymenia dubyi. Under Pu mmerer reaction conditions (TFAA/Pyr), 2 yielded the 5-oxo-L-pipecolic acid derivative 6.