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Direct Organocatalytic Asymmetric Aldol Reactions of α-Amino Aldehydes: Expedient Syntheses of Highly Enantiomerically Enriched a nti -β-Hydroxy-α-amino Acids

2004; American Chemical Society; Volume: 6; Issue: 20 Linguagem: Inglês

10.1021/ol0485417

1523-7060

Rajeswari Thayumanavan, Fujie Tanaka, Carlos F. Barbas,

Synthetic Organic Chemistry Methods

A simple and efficient method for the synthesis of highly enantiomerically enriched β-hydroxy-α-amino acid derivatives has been developed. Direct asymmetric aldol reactions of a glycine aldehyde (aminoacetaldehyde) derivative have been performed under organocatalysis using l-proline or (S)-5-pyrrolidine-2-yl-1H-tetrazole. The reactions afforded anti-β-hydroxy-α-amino aldehydes in good yield with high diastereoselectivity (dr up to >100:1) and high enantioselectivity (up to >99.5% ee), which were easily transformed into β-hydroxy-α-amino acid derivatives.