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Synthesis 2010(11): 1891-1898  
DOI: 10.1055/s-0029-1218753
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Cyclodehydration of Fluorinated Diols Using the Mitsunobu Reaction: Highly Efficient Synthesis of Trifluoromethylated Cyclic Ethers

G. K. Surya Prakash*, Clement Do, Fang Wang, Thomas Mathew, George A. Olah*
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA
e-Mail: gprakash@usc.edu;
Further Information

Publication History

Received 5 March 2010
Publication Date:
23 April 2010 (online)

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Abstract

Synthesis of trifluoromethylated cyclic ethers has been achieved via the Mitsunobu cyclodehydration of fluorinated diols with high efficacy. The methodology is found to be widely applicable to the synthesis of cyclic ethers with varying ring size (3-7) from fluorinated diols of differing acidities and steric demands. Cyclic ethers with considerable ring strain can be achieved in moderate yields by this protocol. The methodology is suitable for both primary and secondary alcohols as well as benzylic and aliphatic alcohols as electrophiles to afford the corresponding products in moderate to good yields.

Key words

cyclic ethers - Mitsunobu reaction - trifluoromethylation - stereoselectivity - inversion of configuration

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