Stereoselective synthesis of 3,4-disubstituted pyroglutamates by ring transformation of 5-ylidene-1,3-diosan-4-ones with N-(diphenylmethylene)-glycinate

Authors
Ali, A Ahmad, VU Ziemer, B Liebscher, J
Citation
A. Ali et al., Stereoselective synthesis of 3,4-disubstituted pyroglutamates by ring transformation of 5-ylidene-1,3-diosan-4-ones with N-(diphenylmethylene)-glycinate, TETRAHEDR-A, 11(21), 2000, pp. 4365-4375
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
21
Year of publication
2000
Pages
4365 - 4375
Database
ISI
SICI code
0957-4166(20001103)11:21<4365:SSO3PB>2.0.ZU;2-4
Abstract
N-(Diphenylmethylene)-glycinate gives stereoselective conjugate addition to readily available (E) and (Z)-5-ylidene-1,3-dioxan-4-ones. Hydrolytic clea vage of the imine functionality of the resulting Michael-adducts causes rin g transformation to new, optically active 3,4-disubstituted pyroglutamates. (C) 2000 Elsevier Science Ltd. All rights reserved.