Tetrahedron Asymmetry p. 1083 - 1099 (1997)
Update date:2022-08-29
Topics:
Carpentier, Jean-Francois
Mortreux, Andre
The enantioselective hydrogenation of several α-keto esters (3a-f, 5a-j), α-keto amides (7a-e) and isatine derivatives (9a-d) with a set of four representative neutral homogeneous rhodium-amidophosphine-phosphinite catalysts has been investigated. Trifluoroacetate-Rh-AMPP catalytic precursors promoted the rapid, efficient synthesis of aliphatic α-hydroxy esters 4a-f in moderate to high enantioselectivities (66-95% eel, in contrast to most aromatic α-hydroxy esters 6a-j (8-81% eel. Best enantioselectivities for α-hydroxy amides 8a-e (85-95% eel and dioxindoIes 10a-d (80-94% eel were obtained with chloro-Rh-AMPP precursors. It is proposed that, contrary to α-keto amides, α-keto esters do not chelate onto the rhodium center and that, in such circumstances, the asymmetric induction is mainly controlled by the steric hindrance around the C=O function.
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