ALLYLIC TIN(IV)-TIN(II) CHLORIDE-ACETONITRILE AS A NOVEL SYSTEM FOR ALLYLATION OF CARBONYLS OR IMINES

Authors
YASUDA M SUGAWA Y YAMAMOTO A SHIBATA I BABA A
Citation
M. Yasuda et al., ALLYLIC TIN(IV)-TIN(II) CHLORIDE-ACETONITRILE AS A NOVEL SYSTEM FOR ALLYLATION OF CARBONYLS OR IMINES, Tetrahedron letters, 37(33), 1996, pp. 5951-5954
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
33
Year of publication
1996
Pages
5951 - 5954
Database
ISI
SICI code
0040-4039(1996)37:33<5951:ATCAAN>2.0.ZU;2-L
Abstract
Effective allylation of aldehydes, ketones and imines was accomplished by allylic tributyltins 1 in the presence of SnCl2 in an acetonitrile solution. In this reaction system, Sn(IV)-Sn(II) transmetallation mus t play a key role. generating the allylic tin(II) reagents as a novel reacting species, Acetonitrile effectively promoted the transmetallati on to give anti-adducts in the reaction with cinnamyltin 1c. whereas d ichloromethane disturbed the transmetallation to produce syn-adducts. Copyright (C) 1996 Elsevier Science Ltd