A highly stereocontrolled route to 2-(2′-oxiranyl)piperidines and pyrrolidines: enantioselective synthesis of (+)-α-conhydrine

  • Rodríguez D
  • Picó A
  • Moyano A
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Abstract

The first enantio- and diastereoselective approach to both 2-(2′-oxiranyl)piperidines and to 2-(2′-oxiranyl)pyrrolidines is reported. The method relies on the Sharpless asymmetric epoxidation of allyl alcohols as the sole source of chirality, and involves as the key step the base-mediated cyclization of (α-aminoalkyl)oxiranes functionalized at the ε{lunate} (or δ) position. The asymmetric synthesis of (+)-α-conhydrine illustrates the applicability of this strategy to the preparation of biologically active 2-(1-hydroxyalkyl)piperidine alkaloids. © 2008 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • Alkaloids
  • Asymmetric synthesis
  • Oxiranes
  • Piperidines
  • Pyrrolidines
  • Stereoselectivity

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Authors

  • Dídac Rodríguez

  • Anna Picó

  • Albert Moyano

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