Diastereoselective Synthesis of Hexahydropyrrolo[2,1-b]oxazoles by a Rhodium-Catalyzed Hydroformylation / Silica-Promoted Deformylation Sequence

Authors

  • Maxym Vasylyev Dr.,

    1. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5 (Canada), Fax: (+1) 613-562-5871
    Search for more papers by this author
  • Howard Alper Prof. Dr.

    1. Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5 (Canada), Fax: (+1) 613-562-5871
    Search for more papers by this author

  • We are grateful to the Natural Sciences and Engineering Research Council of Canada for support of the research.

Abstract

Fleetingly formyl: A new rhodium-catalyzed hydroformylation reaction of N-allyl oxazolidines, carried out under a CO/H2 atmosphere, followed by a diastereoselective deformylative cyclization affords hexahydropyrrolo[2,1-b]oxazoles in good yields. The reaction proceeds by a unique hydroformylation–deformylation sequence in which the formyl group virtually substitutes for the {CH2[BOND]O} fragment of the oxazolidine heterocycle.

original image

Ancillary