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Synlett 2001; 2001(6): 0866-0868
DOI: 10.1055/s-2001-14593
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A New Access to Polyhydroxylated Pyrrolidines from Epoxyaldehydes

Tahar Ayad* , Yves Génisson, Michel Baltas, Liliane Gorrichon
  • *Synthèse et Physicochimie de Molécules d'Intérêt Biologique, UMR 5068 CNRS-Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse cedex 04, France; Fax + 33-(0) 5 61 55 60 11; E-mail: genisson@ramses.ups-tlse.fr; baltas@iris.ups-tlse.fr
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Publication History

Publication Date:
31 December 2001 (online)

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Our approach relies on the stereocontrolled vinylation of a chiral α,β-epoxyimine derived from the corresponding aldehyde. Regioselective opening of the oxirane with carbonate anion allowed the formation of an oxazolidinone intermediate from which the glucosidase inhibitor 1,4-dideoxy-1,4-imino-d-glucitol (14) was synthesised. Direct cyclisation into a 2-vinyl-3,4-epoxypyrrolidine afforded a valuable intermediate for the preparation of synthetic azasugar analogues.

asymmetric synthesis - azasugars - epoxides - imines - 1,4-dideoxy-1,4-imino-d-glucitol