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Angew Chem Int Ed Engl. 2014 Mar 17;53(12):3236-40. doi: 10.1002/anie.201309634. Epub 2014 Feb 19.

Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds.

Author information

1
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578 (Japan).

Abstract

The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds.

KEYWORDS:

amino alcohol; chemoselectivity; copper; oxidation; radical chemistry

PMID:
24554411
DOI:
10.1002/anie.201309634
[Indexed for MEDLINE]

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