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Short Reports • J. Braz. Chem. Soc. 15 (6) • Dec 2004 • https://doi.org/10.1590/S0103-50532004000600027   copy

An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones

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Reduction of beta-enamino ketones 2 with NaBH4 in glacial acetic acid gave gamma-amino alcohols 1 in 70% to 98% yield with diastereomeric excesses, preferentially the syn product, from 44% to 90%. The stereochemistry of these compounds was confirmed by analysis of their tetrahydro-1,3-oxazine derivatives 3.

amino alcohols; enamino ketones; oxazines; stereoselective reduction

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