Synthesis
DOI: 10.1055/s-0036-1588521
paper
© Georg Thieme Verlag Stuttgart · New York

Desymmetrization of Hepta-1,6-dien-4-ol by a Highly Stereo­selective Tandem Prins–Ritter Cyclization: Access to New THP Acetamides

Thomas Glachet, Fabienne Fache, Béatrice Pelotier, Olivier Piva*
  • Univ Lyon, Université Claude Bernard Lyon 1, CNRS, INSA Lyon, CPE Lyon, ICBMS, UMR 5246, 69622 Villeurbanne Cedex, France   Email: olivier.piva@univ-lyon1.fr
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Publication History

Received: 10 May 2017

Accepted after revision: 05 July 2017

Publication Date:
14 August 2017 (eFirst)

Abstract

Prins–Ritter cyclization performed from hepta-1,6-dien-4-ol and various aldehydes, promoted by bismuth(II) triflate, afforded N-(tetrahydropyranyl)acetamides in moderate to high yields. Subsequent Wacker-type oxidation using Dess–Martin periodinane (DMP) delivered the corresponding ketones.

Supporting Information