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Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

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.

SUBMITTER: Guo F

PROVIDER: S-EPMC3073418 | biostudies-literature | 2011 Jan

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

Guo Fenghai F Konkol Leah C LC Thomson Regan J RJ

Journal of the American Chemical Society 20101209 1

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. ...[more]

PMID: 21141997

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