Origins of Selectivity and General Model for Chiral Phosphoric Acid-Catalyzed Oxetane Desymmetrizations

Pier Alexandre Champagne; K. N. Houk

doi:10.1021/jacs.6b08276

Origins of Selectivity and General Model for Chiral Phosphoric Acid-Catalyzed Oxetane Desymmetrizations

Pier Alexandre Champagne
, K. N. Houk

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

54 Scopus citations

Abstract

The origins of the high enantioselectivity of chiral phosphoric acid-catalyzed oxetane desymmetrizations were investigated by density functional theory (DFT) calculations. Distortion of the catalyst structure, caused by steric crowding in the catalyst pocket of one enantiomeric transition state, is the main cause for stereochemical preference. A general model was developed to assist in the rational design of new catalysts for related transformations.

Original language	English (US)
Pages (from-to)	12356-12359
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	38
DOIs	https://doi.org/10.1021/jacs.6b08276
State	Published - Sep 28 2016
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.6b08276

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abstract = "The origins of the high enantioselectivity of chiral phosphoric acid-catalyzed oxetane desymmetrizations were investigated by density functional theory (DFT) calculations. Distortion of the catalyst structure, caused by steric crowding in the catalyst pocket of one enantiomeric transition state, is the main cause for stereochemical preference. A general model was developed to assist in the rational design of new catalysts for related transformations.",

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AB - The origins of the high enantioselectivity of chiral phosphoric acid-catalyzed oxetane desymmetrizations were investigated by density functional theory (DFT) calculations. Distortion of the catalyst structure, caused by steric crowding in the catalyst pocket of one enantiomeric transition state, is the main cause for stereochemical preference. A general model was developed to assist in the rational design of new catalysts for related transformations.

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Origins of Selectivity and General Model for Chiral Phosphoric Acid-Catalyzed Oxetane Desymmetrizations

Abstract

All Science Journal Classification (ASJC) codes

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