Cp2VCl2-catalyzed meso-selective pinacol coupling reaction of aldimines inthe presence of chlorosilane and zinc metal

Citation
B. Hatano et al., Cp2VCl2-catalyzed meso-selective pinacol coupling reaction of aldimines inthe presence of chlorosilane and zinc metal, J ORG CHEM, 63(25), 1998, pp. 9421-9424
Citations number
42
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
63
Issue
25
Year of publication
1998
Pages
9421 - 9424
Database
ISI
SICI code
0022-3263(199812)63:25<9421:CMPCRO>2.0.ZU;2-B
Abstract
A catalytic reductive coupling of aldimines was achieved by using a catalys t Cp2VCl2/PhMe2SiCl/Zn system. The influence of the catalyst, chlorosilane, co-reductant, solvent, and temperature on both the yield and diastereosele ctivity of the coupling products was investigated in detail. As a result, t he present Cp2VCl2-catalyzed reductive coupling of aldimines in the presenc e of PhMe2SiCl and zinc metal provided the corresponding 1,2-diamines in go od yield with high meso selectivity (up to 92% meso), while the reductive c oupling of aldehydes, ketones, and aldimines by the hitherto known catalyti c methods leads to the preferential formation of dl isomers of the coupling products.