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Enantioselective Synthesis of Biphenols from 1,4-Diketones by Traceless Central-to-Axial Chirality Exchange

Year: 2010

Type: article

Abstract: A method for the enantioselective synthesis of biphenols from readily prepared 1,4-diketones is reported. Key to the success of this method is the highly selective transfer of central to axial chirality during a double aromatization event triggered by BF(3)·OEt(2). On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja108717r

Authors: Fenghai Guo, Leah C. Konkol, Regan J. Thomson

Institution: Northwestern University

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Award: New Methods for the Concise Synthesis of Bioactive Polycyclic Molecules