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A Novel Method for the Asymmetric Synthesis of α,α-Disubstituted Alkylamines via Grignard Additions to Ketimines

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journal contribution
posted on 08.08.1997, 00:00 by Denice M. Spero, Suresh R. Kapadia
The design of practical methods to prepare optically pure α,α-disubstituted alkylamines remains an important challenge. We now report a new and efficient method for the asymmetric synthesis of α,α-disubstituted amines 2 where R3 is a nitrogen-containing heterocycle. The method utilizes the diasteroselective addition of a Grignard reagent to ketimine 1, followed by an oxidative cleavage of the chiral auxiliary to afford the target amines 2 in high enantiomeric excess. A model involving chelation of the imine and heterocyclic nitrogen with Mg is proposed to rationalize the observed diastereoselectivity.