Patent Number: 7,087,789

Title: Methods for nucleophilic fluoromethylation

Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO.sub.2CF.sub.3 (or sulfoxide PhSOCF.sub.3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (".sup.-CF2.sup.-"), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.

Inventors: Prakash; G. K. Surya (Hacienda Heights, CA), Hu; Jinbo (Los Angeles, CA), Olah; George A. (Beverly Hills, CA)

Assignee: University of Southern California

International Classification: C07C 319/00 (20060101)

Expiration Date: 8/08/02018