Triflimide-catalyzed allylsilane annulations of benzylic alcohols for the divergent synthesis of indanes and tetralins

Jordan C.T. Reddel, Weiwei Wang, Kalli Koukounas, Regan J. Thomson*

*Corresponding author for this work

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

The development of a triflimide-catalyzed annulation of benzylic alcohols with allylsilanes for the synthesis of indane or tetralin structures is reported. In this fragment coupling reaction, complexity is built rapidly from readily available starting materials to yield diverse sets of products with up to three contiguous stereocenters. Indanes or tetralins can be generated from common precursors depending on the structure of the allylsilane reagent used. The concise synthesis of several lignan natural products highlights the utility of this newly devised methodology.

Original languageEnglish (US)
Pages (from-to)2156-2160
Number of pages5
JournalChemical Science
Volume8
Issue number3
DOIs
StatePublished - Jan 1 2017

ASJC Scopus subject areas

  • Chemistry(all)

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