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

Chemical Science
Jordan C T ReddelRegan J Thomson

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.

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Citations

May 6, 2017·Organic Letters·Xiao CaiBenjamin J Stokes
Aug 30, 2019·The Journal of Organic Chemistry·Meng-Yang ChangHsing-Yin Chen
Jan 6, 2018·Journal of the American Chemical Society·Matthew R PorterJoseph J Topczewski
Sep 27, 2018·Chemical Reviews·Wanxiang Zhao, Jianwei Sun

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Methods Mentioned

BETA
column chromatography

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