4.4 Article

A Sakurai-Prins-Ritter reaction sequence for the diastereoselective synthesis of 4-amidotetrahydropyrans catalyzed by bismuth triflate

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 40, Pages 5727-5731

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.07.079

Keywords

tetrahydropyrans; diastereoselectivity; aldehydes; allyltrimethylsilane; Bi(OTf)(3)center dot 4H(2)O; Sakurai-Prins-Ritter

Funding

  1. CSIR, New Delhi

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The synthesis of 4-amidotetrahydropyrans has been achieved by a single-step Sakurai-Prins-Ritter reaction sequence in a domino fashion by the reaction of an aldehyde and allyltrimethylsilane in acetonitrile using Bi(OTf)(3) as catalyst. The present synthesis is highly efficient and diastereoselective. (C) 2008 Elsevier Ltd. All rights reserved.

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