SYNTHESIS OF ENANTIOENRICHED 4-THIAZOLIDINONE (-)-LY213829 BY CHEMOSELECTIVE BENZYLAMIDE CLEAVAGE IN THE PRESENCE OF A C-S BOND

Authors
HANSEN MM HARKNESS AR KHAU VV MARTINELLI MJ DEETER JB
Citation
Mm. Hansen et al., SYNTHESIS OF ENANTIOENRICHED 4-THIAZOLIDINONE (-)-LY213829 BY CHEMOSELECTIVE BENZYLAMIDE CLEAVAGE IN THE PRESENCE OF A C-S BOND, Tetrahedron : asymmetry, 7(9), 1996, pp. 2515-2518
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
9
Year of publication
1996
Pages
2515 - 2518
Database
ISI
SICI code
0957-4166(1996)7:9<2515:SOE4(B>2.0.ZU;2-O
Abstract
(R)-2-Methylbenzylamine has been used to covalently ''resolve'' thiol acid 7 and assemble 4-thiazolidinone 8a in one step. Selective deprote ction of the 2-methylbenzylamide using lithium in ammonia/THF has been achieved in the presence of a readily hydrogenolyzed C-S bond. Enanti oenriched (-)-LY213829 (1) of 98% ee has been prepared by this five st ep route in 25% yield from aldehyde 2. Copyright (C) 1996 Elsevier Sci ence Ltd