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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 .