Stereoselective Monofluoromethylation of Primary and Secondary Alcohols by Using a Fluorocarbon Nucleophile in a Mitsunobu Reaction

Abstract

OH is exchanged: An efficient Mitsunobu reaction that uses a fluorinated carbon pronucleophile for the facile synthesis of monofluoromethyl derivatives of alcohols is reported (see scheme; DIAD=diisopropyl azodicarboxylate). This reaction can be performed under mild conditions and is highly feasible for primary, secondary, allylic, benzylic, and alicyclic alcohols. Excellent enantiospecificity is observed for chiral alcohols. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z700834_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.