Difluoromethyl Phenyl Sulfone as a Selective Difluoromethylene Dianion Equivalent: One‐Pot Stereoselective Synthesis of  anti‐ 2,2‐Difluoropropane‐1,3‐diols | Zendy

Prakash G. K. Surya | Zendy; Hu Jinbo | Zendy; Mathew Thomas | Zendy; Olah George A. | Zendy

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Difluoromethyl Phenyl Sulfone as a Selective Difluoromethylene Dianion Equivalent: One‐Pot Stereoselective Synthesis of anti‐ 2,2‐Difluoropropane‐1,3‐diols

Author(s) -

Prakash G. K. Surya,

Hu Jinbo,

Mathew Thomas,

Olah George A.

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200352172

Subject(s) - sulfone , stereoselectivity , steric effects , intramolecular force , chemistry , charge (physics) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , physics , quantum mechanics

Intramolecular charge–charge repulsion rather than traditional steric control is responsible for the high diastereoselectivity (up to 94 % de ) obtained in t BuOK‐induced difluoromethylenation of aldehydes 1 with difluoromethyl phenyl sulfone ( 2 ) to give symmetrical and unsymmetrical anti ‐2,2‐difluoropropane‐1,3‐diols 3 .

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