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

Fenghai Guo; Leah C. Konkol; Regan J. Thomson

doi:10.1021/ja108717r

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

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

Chemistry

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

141 Scopus citations

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 BF₃·OEt₂. On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.

Original language	English (US)
Pages (from-to)	18-20
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	133
Issue number	1
DOIs	https://doi.org/10.1021/ja108717r
State	Published - Jan 12 2011

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja108717r

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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 BF3·OEt2. On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.",

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

Abstract

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CCDC 840106: Experimental Crystal Structure Determination

CCDC 840104: Experimental Crystal Structure Determination

CCDC 840105: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 840106: Experimental Crystal Structure Determination

CCDC 840104: Experimental Crystal Structure Determination

CCDC 840105: Experimental Crystal Structure Determination

Cite this