One-pot synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans using lithiation-borylation, allylation and Prins cyclisation reactions

Adeem Mahmood, Jose Ramon Suarez, Stephen P. Thomas, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

2,3,4,5,6-Pentasubstituted tetrahydropyrans have been prepared in good yield (42-57%) with excellent dr (>95:5) and er (>95:5) using a one-pot lithiation-borylation, allylation and Prins cyclisation reaction. (C) 2012 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)49-51
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number1
Early online date26 Oct 2012
DOIs
Publication statusPublished - 2 Jan 2013

Keywords

  • Lithiation-borylation
  • Allylation
  • Prins cyclisation
  • Tandem
  • Boronic ester
  • STEREOCONTROLLED SYNTHESIS
  • STEREOSELECTIVE-SYNTHESIS
  • BORONIC ESTERS
  • ETHERS
  • ALDEHYDES
  • ALCOHOLS
  • BORANES
  • HYDROBORATION
  • DIHYDROPYRANS
  • REARRANGEMENT

Access to Document

  • AggarwalTHPMnuscript

    NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters . Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters 54 (2013) 49–5, DOI 10.1016/j.tetlet.2012.10.091

    Accepted author manuscript, 436 KB

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