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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