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

Benito Alcaide; Pedro Almendros; Gema Cabrero; M. Pilar Ruiz

doi:10.1055/s-2008-1067224

PSP

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 Cabrero^a, M. Pilar Ruiz^a
^a Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain
Fax: +34(91)3944103; e-Mail: alcaideb@quim.ucm.es;
^b Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain
Fax: +34(91)5644853; e-Mail: Palmendros@iqog.csic.es;

Abstract

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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.

Key words

catalysis - iodine - β-lactams - pyrrolidines - ring expansion

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References

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