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Stereoselective Organocatalytic Synthesis of α,α-Difluoro-γ,γ-Disubstituted Butenals

Satoru Arimitsu* and Makoto Nakasone

*Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Senbaru 1, Nishihara, Nakagami, Okinawa 903-0123, Japan, Email: arimitsusci.u-ryukyu.ac.jp

S. Arimitsu, M. Nakasone, J. Org. Chem., 2016, 81, 6707-6713.

DOI: 10.1021/acs.joc.6b01334 (free Supporting Information)



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Abstract

An organocatalytic system of L-proline and salicylic acid enables a highly stereoselective synthesis of α,α-difluoro-γ,γ-disubstituted butenals. The reaction offers a wide substrate scope and excellent E stereoselectivity in most cases.

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Key Words

allyl fluorides, fluoroaldehydes, NFSI, sodium borohydride


ID: J42-Y2016