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A straightforward approach towards combined ?-amino and ?-hydroxy acids based on Passerini reactions.

ABSTRACT: Complex amino acids with an ?-acyloxycarbonyl functionality in the side chain are easily available through epoxide opening by chelated enolates and subsequent oxidation/Passerini reaction. This protocol works with both, aldehyde and ketone intermediates, as long as the ketones are activated by electron-withdrawing groups. In principle Ugi reactions are also possible, allowing the generation of diamino acid derivatives.

SUBMITTER: Zahoor AF

PROVIDER: S-EPMC3182440 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions.

Zahoor Ameer F AF Thies Sarah S Kazmaier Uli U

Beilstein journal of organic chemistry 20110919

Complex amino acids with an α-acyloxycarbonyl functionality in the side chain are easily available through epoxide opening by chelated enolates and subsequent oxidation/Passerini reaction. This protocol works with both, aldehyde and ketone intermediates, as long as the ketones are activated by electron-withdrawing groups. In principle Ugi reactions are also possible, allowing the generation of diamino acid derivatives. ...[more]

PMID: 21977215

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