ALLYLATION OF UNACTIVATED KETONES BY TETRAALLYLTIN ACCELERATED BY PHENOL - APPLICATION TO ASYMMETRIC ALLYLATION USING A TETRAALLYLTIN-BINOLSYSTEM

Authors
YASUDA M KITAHARA N FUJIBAYASHI T BABA A
Citation
M. Yasuda et al., ALLYLATION OF UNACTIVATED KETONES BY TETRAALLYLTIN ACCELERATED BY PHENOL - APPLICATION TO ASYMMETRIC ALLYLATION USING A TETRAALLYLTIN-BINOLSYSTEM, Chemistry Letters, (8), 1998, pp. 743-744
Citations number
36
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
8
Year of publication
1998
Pages
743 - 744
Database
ISI
SICI code
0366-7022(1998):8<743:AOUKBT>2.0.ZU;2-C
Abstract
The tetraallyltin-phenol system was mild and effective for allylation of unactivated ketones, giving tertiary alcohols in high yields. The a symmetric allylation was achieved by a tetraallyltin-homochiral BINOL (1,1'-bi-2-naphthol) system. The addition of methanol raised the enant ioselectivity to afford the tertiary homoallylic alcohol up to 60% ee.