A NEW CHIRAL AUXILIARY IN ENANTIOSELECTIVE HYDROGENATIONS - (-)-DIHYDROVINPOCETINE .1. HYDROGENATION OF ISOPHORONE

Authors
TARNAI T TUNGLER A MATHE T PETRO J SHELDON RA TOTH G
Citation
T. Tarnai et al., A NEW CHIRAL AUXILIARY IN ENANTIOSELECTIVE HYDROGENATIONS - (-)-DIHYDROVINPOCETINE .1. HYDROGENATION OF ISOPHORONE, Journal of molecular catalysis. A, Chemical, 102(1), 1995, pp. 41-47
Citations number
10
Categorie Soggetti
Chemistry Physical
Journal title
Journal of molecular catalysis. A, Chemical → ACNP
ISSN journal
13811169
Volume
102
Issue
1
Year of publication
1995
Pages
41 - 47
Database
ISI
SICI code
1381-1169(1995)102:1<41:ANCAIE>2.0.ZU;2-A
Abstract
A vinca-type synthetic alkaloid:(-)-dihydrovinpocetine is a promising chiral auxiliary in the enantioselective hydrogenation of the prochira l C=C bond of isophorone. Various catalytic metals and supports have b een screened. The effect of acidic additives is described. The highest optical yield (38%) is obtained with a Pd black catalyst. Mechanistic considerations and comparison with the known Pt/cinchona system have been made.