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

doi:10.1039/c6sc04762a

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

Chemistry

Research output: Contribution to journal › Article › peer-review

25 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 language	English (US)
Pages (from-to)	2156-2160
Number of pages	5
Journal	Chemical Science
Volume	8
Issue number	3
DOIs	https://doi.org/10.1039/c6sc04762a
State	Published - 2017

Funding

We thank support in part from the NSF (CHE1361173) and Northwestern University. We gratefully acknowledge the award of a CLP Lambert Fellowship to KK.

ASJC Scopus subject areas

General Chemistry

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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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AU - Reddel, Jordan C.T.

AU - Wang, Weiwei

AU - Koukounas, Kalli

AU - Thomson, Regan J.

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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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JF - Chemical Science

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

Abstract

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