Proline-Catalyzed Enantioselective Synthesis of Aza-Quaternary Carbon Derivatives

Abstract

2-Aryl-3H-indol-3-ones reacted with aldehydes or ketones in the presence of l-proline as a catalyst to give the corresponding aza-quaternary carbon addition product in good yield with moderate to excellent regioselectivity and enantioselectivity. The system was applied to the reaction of 2-(2-bromo-phenyl)-3H-indol-3-one and acetaldehyde to give 2-[2-(2-bromophenyl)-3-oxoindolin-2-yl]acetaldehyde, which is a precursor for the synthesis of some alkaloids such as hinckdentine A.

Key words

aza-quaternary carbon - proline - Mannich reaction - hinckdentine A

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CCDC 815953 (for 3h) and CCDC 815954 (for 3c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/deposit [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax [phone]; email: [e-mail]].