Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5263354 | Tetrahedron Letters | 2014 | 4 Pages |
Abstract
The Horner-Wadsworth-Emmons reactions of ethyl 2-fluoro-2-diethylphosphonoacetate with 2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)cyclopentanone (2-OBO-cyclopentanone) using n-butyllithium furnished the corresponding tetra-substituted fluoroolefin in an E-selective manner (E:Z = 95:5). A facile synthesis of rac-N-Cbz-Gly-Ψ[(E)-CFC]-Pro-OH as a dipeptide isostere was achieved based on the E-selective Horner-Wadsworth-Emmons reaction.
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Authors
Shigeki Sano, Tomoya Matsumoto, Michiyasu Nakao,