Title of article
Z-Selective Horner–Wadsworth–Emmons reaction of 2-TOM-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(Z)-CFC]-Pro-OH dipeptide isostere
Author/Authors
Sano، نويسنده , , Shigeki and Matsumoto، نويسنده , , Tomoya and Nanataki، نويسنده , , Hiroshi and Tempaku، نويسنده , , Shota and Nakao، نويسنده , , Michiyasu، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2014
Pages
4
From page
6248
To page
6251
Abstract
The Horner–Wadsworth–Emmons reactions of 2-fluoro-2-diethylphosphonoacetic acid with 2-{[(triisopropylsilyl)oxy]methyl}cyclopentanone (2-TOM-cyclopentanone) using methylmagnesium chloride furnished the corresponding tetra-substituted fluoroolefin in a Z-selective manner (E/Z = 9:91). A facile synthesis of rac-N-Cbz-Gly-Ψ[(Z)-CFC]-Pro-OH as a dipeptide isostere was achieved based on the Z-selective Horner–Wadsworth–Emmons reaction.
Keywords
proline , Grignard reagent , Horner–Wadsworth–Emmons reaction , Z-Selective , Fluoroolefin
Journal title
Tetrahedron Letters
Serial Year
2014
Journal title
Tetrahedron Letters
Record number
1891152
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