Citation
Asy. Lee et Cw. Wu, Stannyl-oriented regioselective allylation and its application to the synthesis of silyl misoprostol, TETRAHEDRON, 55(43), 1999, pp. 12531-12542
Citations number
50
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020
→ ACNP
Volume
55
Issue
43
Year of publication
1999
Pages
12531 - 12542
Database
ISI
SICI code
0040-4020(19991022)55:43<12531:SRAAIA>2.0.ZU;2-U
Abstract
A mixture of Zn, CeCl3, 3-bromo-1-tributylstannylpropene and aldehyde or ke
tone in THF/PhH (v/v=9/1) was sonicated in a commercial cleaning bath. delt
a-Tributylstannylhomoallyl alcohol was produced as the sole regioselective
product and (E)-stereoisomer was formed as major adduct. Silyl Misoprostol
was synthesized by the coupling reaction of cyclopentenone and stannylhomoa
llyl alcohol. (C) 1999 Elsevier Science Ltd. All rights reserved.