Z-Selective Horner-Wadsworth-Emmons reaction of 2-TOM-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[Z)-CF=C1-Pro-OH dipeptide isostere

被引：12

作者：

Sano, Shigeki ^{[1
]}

Matsumoto, Tomoya ^{[1
]}

Nanataki, Hiroshi ^{[1
]}

Tempaku, Shota ^{[1
]}

Nakao, Michiyasu ^{[1
]}

机构：

[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 45期

关键词：

Horner-Wadsworth-Emmons reaction; Fluoroolefin; Proline; Grignard reagent; Z-selective; PEPTIDASE-IV; FLUOROOLEFIN; INHIBITION; ALDEHYDES;

D O I：

10.1016/j.tetlet.2014.09.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Horner-Wadsworth-Emmons reactions of 2-fluoro-2-diethylphosphonoacetic acid with 241(triisopropylsilyl)oxy]methyl)cyclopentanone (2-TOM-cyclopentanone) using methylrnagnesium chloride furnished the corresponding tetra-substituted fluoroolefin in a Z-selective manner (E/Z = 9:91). A facile synthesis of rac-N-Cbz-Gly-Psi[(Z)-CF=C]-Pro-OH as a dipeptide isostere was achieved based on the Z-selective Horner-Wadsworth-Emmons reaction. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6248 / 6251

页数：4

共 29 条

[1] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].