Enantiomerically Enriched Allylic Alcohols and Allylic Amines via C–C Bond-Forming Hydrogenation: Asymmetric Carbonyl and Imine Vinylation
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- 5 September 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Accounts of Chemical Research
- Vol. 40 (12) , 1394-1401
- https://doi.org/10.1021/ar7001123
Abstract
Hydrogenation of alkynes in the presence of carbonyl compounds and imines using cationic rhodium(I) and iridium(I) precatalysts enables the formation of allylic alcohols and allylic amines, respectively. Through the use of hydrogenation catalysts modified by chiral ligands, allylic alcohols and allylic amines may be generated in highly optically enriched forms. Hydrogenative fragment couplings of this type circumvent the use of preformed organometallic reagents and avoid the generation of stoichiometric byproducts.Keywords
This publication has 100 references indexed in Scilit:
- Catalytic Asymmetric Vinylation of KetonesJournal of the American Chemical Society, 2004
- Asymmetric Alkylation of N-Toluenesulfonylimines with Dialkylzinc Reagents Catalyzed by Copper−Chiral AmidophosphineThe Journal of Organic Chemistry, 2003
- Three‐Component Enantioselective Synthesis of Propargylamines through Zr‐Catalyzed Additions of Alkyl Zinc Reagents to AlkynyliminesAngewandte Chemie International Edition in English, 2003
- Copper−Amidophosphine Catalyst in Asymmetric Addition of Organozinc to IminesJournal of the American Chemical Society, 2000
- Catalytic Asymmetric Addition of ZnPh2 to Ketones: Enantioselective Formation of Quaternary StereocentersJournal of the American Chemical Society, 1998
- Extremely Chemoselective Silylformylation and Silylcarbocyclization of AlkynalsJournal of the American Chemical Society, 1994
- Organoyttrium-catalyzed cyclization of substituted 1,5- and 1,6-dienesJournal of the American Chemical Society, 1992
- Directed Homogeneous Hydrogenation [New Synthetic Methods (65)]Angewandte Chemie International Edition in English, 1987
- Triarylphosphine, hydride, and ethylene complexes or rhodium(I) chlorideJournal of the American Chemical Society, 1974
- Über die Synthese höherer Glieder der aliphatischen Reihe aus KohlenoxydBerichte der deutschen chemischen Gesellschaft (A and B Series), 1923