NEW STRATEGY FOR THE SYNTHESIS OF 3-SUBSTITUTED PROLINES

Authors
KAROYAN P CHASSAING G
Citation
P. Karoyan et G. Chassaing, NEW STRATEGY FOR THE SYNTHESIS OF 3-SUBSTITUTED PROLINES, Tetrahedron letters, 38(1), 1997, pp. 85-88
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
1
Year of publication
1997
Pages
85 - 88
Database
ISI
SICI code
0040-4039(1997)38:1<85:NSFTSO>2.0.ZU;2-A
Abstract
Ring formation involving a Sere trig cyclization between a zinc enolat e and a non activated double bond led to cis diastereoisomer of 3-subs tituted prolines. This cyclization was achieved with transfer of chira lity onto the C-2 carbon when nitrogen was protected by an alpha-methy lbenzyl group. Reprotonation of the lithium enolate of cis derivative yielded the trans diastereoisomer. Copyright (C) 1996 Published by Els evier Science Ltd