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Conjugate addition of lithium (S)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha, beta-unsaturated Weinreb amides proceeds with high levels of diastereoselectivity (>95% de). The beta-amino Weinreb amide products may be transformed into beta-amino ketones via reactions with Grignard reagents, while treatment with DIBAL-H furnishes beta-amino aldehydes. Trapping of the aldehyde via Wadsworth-Emmons reaction and subsequent manipulation offers an efficient route to homochiral delta-amino acid derivatives and 2-substituted piperidines. The application of this methodology for the synthesis of (S)-coniine is demonstrated.

Original publication

DOI

10.1039/b402531h

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/05/2004

Volume

2

Pages

1387 - 1394

Keywords

Aldehydes, Alkaloids, Amides, Ketones, Lithium Compounds, Molecular Structure, Piperidines