N-(CHLOROMETHYLOXYCARBONYL)PYRROLIDINE AS A SOURCE OF HOCH2- SYNTHON

Authors
GUIJARRO A YUS M
Citation
A. Guijarro et M. Yus, N-(CHLOROMETHYLOXYCARBONYL)PYRROLIDINE AS A SOURCE OF HOCH2- SYNTHON, Tetrahedron letters, 37(31), 1996, pp. 5593-5596
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
31
Year of publication
1996
Pages
5593 - 5596
Database
ISI
SICI code
0040-4039(1996)37:31<5593:NAASOH>2.0.ZU;2-D
Abstract
The reaction of N-(chloromethyloxycarbonyl)pyrrolidine (1) with lithiu m powder and a catalytic amount of DTBB (2.5 mol %) in the presence of different electrophiles [Me(3)SiCl, Bu(i)CHO, Bu(t)CHO, PhCHO, Et(2)C O, (CH2)(5)CO, PhCOMe, Ph(2)CO] in THF at -78 degrees C leads, after h ydrolysis with water, to the expected functionalised carbamates 2. Dep rotection of the acetophenone derivative 2g with DIBALH at THF reflux yields, after hydrolysis, the corresponding 1,2-diol 3g. Copyright (C) 1996 Elsevier Science Ltd