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Synthesis 2006(23): 4060-4064
DOI: 10.1055/s-2006-950346
DOI: 10.1055/s-2006-950346
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New YorkOrganocatalytic Asymmetric α-Aminomethylation of Cyclohexanones
Further Information
Received
28 August 2006
Publication Date:
06 November 2006 (online)
Publication History
Publication Date:
06 November 2006 (online)

Abstract
The amino acid catalyzed direct asymmetric Mannich reaction between aminomethyl ether 1 and cyclohexanones is presented. The unprecedented reaction proceeds via an ionic transition state and gives the corresponding Mannich bases in moderate to high yields with 75-99% ee.
Key words
organocatalysis - Mannich reactions - aminomethylation - amino acids - asymmetric catalysis
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21Neutral aluminum oxide was used, since the Mannich bases 3 racemize during silica gel column chromatography.