Work

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

Year: 2016

Type: article

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.

Source: Chemical Science

DOI: 10.1039/c6sc04762a

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

Institution: Northwestern University

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Science Foundation, Northwestern University, Division of Chemistry

Awards: G3621164616, New Stereoselective Fragment Coupling Reactions for Organic Synthesis