COPPER(I) IODIDE-CATALYZED REGIOSELECTIVE ALLYLATION OF ALPHA-(2-PYRIDYLTHIO)ALLYLSTANNANES - A NEW ROUTE TO DELTA,EPSILON-UNSATURATED KETONES

Authors
TAKEDA T MATSUNAGA K URUGA T TAKAKURA M FUJIWARA T
Citation
T. Takeda et al., COPPER(I) IODIDE-CATALYZED REGIOSELECTIVE ALLYLATION OF ALPHA-(2-PYRIDYLTHIO)ALLYLSTANNANES - A NEW ROUTE TO DELTA,EPSILON-UNSATURATED KETONES, Tetrahedron letters, 38(16), 1997, pp. 2879-2882
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
16
Year of publication
1997
Pages
2879 - 2882
Database
ISI
SICI code
0040-4039(1997)38:16<2879:CIRAOA>2.0.ZU;2-A
Abstract
The reaction of alpha-(2-pyridylthio)allylstannanes with allylic halid es in the presence of a catalytic amount of copper(1) iodide in DMSO-T HF produced the 1,5-dienes 3 in good yields. The gamma-selective allyl ation using allyl chloride followed by the alkylation and hydrolysis o f resulting vinyl sulfides gave delta,epsilon-unsaturated ketones. (C) 1997 Elsevier Science Ltd.