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CATALYTIC ASYMMETRIC HYDROGENATION OF IMINES - USE OF RHODIUM(I)/PHOSPHINE COMPLEXES AND CHARACTERIZATION OF RHODIUM(I)/IMINE COMPLEXES

TitleCATALYTIC ASYMMETRIC HYDROGENATION OF IMINES - USE OF RHODIUM(I)/PHOSPHINE COMPLEXES AND CHARACTERIZATION OF RHODIUM(I)/IMINE COMPLEXES
Publication TypeJournal Article
Year of Publication1991
AuthorsBecalski, AG, Cullen, WR, Fryzuk, MD, James, BR, Kang, GJ, Rettig, SJ
JournalInorganic Chemistry
Volume30
Pagination5002-5008
Date PublishedDec
Type of ArticleArticle
ISBN Number0020-1669
KeywordsACETOPHENONE, HOMOGENEOUS HYDROGENATION, RHODIUM-PHOSPHINE COMPLEXES, SYSTEMS
Abstract

{An in situ Rh(I)(P-P) catalyst formed from [Rh(NBD)Cl]2 and cycphos (P-P = 1,2-bis(diphenylphosphino)-1-cyclohexylethane) effects asymmetric hydrogenation of some commercially important and model imines in 1:1 benzene/methanol under 1000-1500 psig H2 from -25 to +25-degrees-C; a maximum of 91% ee is obtained for ArC(Me) = NCH2Ph (Ar = 4-MeOC6H4) in the presence of iodide cocatalyst at -25-degrees-C. Two [Rh(diphos)(imine)2]BF4 complexes have been isolated (diphos = 1,2-bis(diphenyl-phosphino)ethane): imine 8 = 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline (complex 11) or imine 4 with Ar = 2-MeOC6H4 (complex 16). Complex 11 crystallizes in the triclinic system, space group P1BAR, with a = 12.564 (1) angstrom

URL<Go to ISI>://A1991GX61500027