Synthesis 2008(17): 2835-2839  
DOI: 10.1055/s-2008-1067224
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Synthesis of Protected Enantiopure 5-Cyano-3,4-dihydroxypyrrolidin-2-ones from β-Lactam Aldehydes Catalyzed by Iodine

Benito Alcaide*a, Pedro Almendros*b, Gema Cabreroa, M. Pilar Ruiza
a Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain
Fax: +34(91)3944103; e-Mail: [email protected];
b Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain
Fax: +34(91)5644853; e-Mail: [email protected];
Further Information

Publication History

Received 11 June 2008
Publication Date:
11 August 2008 (online)

Abstract

A single-step catalytic ring-expansion approach from 4-oxoazetidine-2-carbaldehydes to protected enantiopure 5-cyano-3,4-dihydroxypyrrolidin-2-ones has been achieved by the use of the commercially available and inexpensive reagent, molecular iodine, in the presence of tert-butyldimethyl cyanide. Interestingly, the catalyst directs the reaction toward the selective rearrangement reaction of the β-lactam nucleus rather than cyanohydrin formation.

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