Asymmetric hydrogenation of α-keto acid derivatives by rhodium-}amidophosphine-phosphinite{ catalysts
作者： Jean-François Carpentier , André Mortreux
DOI: 10.1016/S0957-4166(97)00078-5
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摘要: Abstract The enantioselective hydrogenation of several α-keto esters ( 3a-f, 5a-j ), amides 7a-e ) and isatine derivatives 9a-d with a set four representative neutral homogeneous rhodium-amidophosphine-phosphinite catalysts has been investigated. Trifluoroacetato-Rh-AMPP catalytic precursors promoted the rapid, efficient synthesis aliphatic α-hydroxy 4a-f in moderate to high enantioselectivities (66–95% ee), contrast most aromatic 6a-j (8–81% ee). Best for 8a-e (85–95% ee) dioxindoles 10a-d (80–94% were obtained chloro-Rh-AMPP precursors. It is proposed that, contrary amides, do not chelate onto rhodium center such circumstances, asymmetric induction mainly controlled by steric hindrance around CO function.
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