Stereoselective formation of (Z)-2-fluoroalkenoates via Julia-Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones

被引：17

作者：

Larnaud, Florent ^{[1
,2
]}

Pfund, Emmanuel ^{[1
,2
]}

Linclau, Bruno ^{[3
]}

Lequeux, Thierry ^{[1
,2
]}

机构：

[1] Univ Caen Basse Normandie, Lab Chim Mol & Thioorgan, UMR CNRS 6507, F-14050 Caen, France

[2] Univ Caen Basse Normandie, ENSICAEN, FR3038, F-14050 Caen, France

[3] Univ Southampton, Southampton SO17 1BJ, Hants, England

来源：

TETRAHEDRON | 2014年 / 70卷 / 35期

关键词：

Fluoroalkenes; Julia-Kocienski reaction; Fluoroalkenoates; Selective synthesis; TANDEM REDUCTION-OLEFINATION; WADSWORTH-EMMONS REACTION; CARBONYL-COMPOUNDS; ALPHA-FLUORO-ALPHA; BETA-UNSATURATED ESTERS; 3,5-BIS(TRIFLUOROMETHYL)PHENYL SULFONES; CONDENSATION; STEP; FLUOROALKENOATES; STEREOCHEMISTRY; CONSTRUCTION;

D O I：

10.1016/j.tet.2014.06.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selective synthesis of fluoroalkenoates is reported from a pyrimidinyl fluorosulfone. This sulfone allowed the preparation of Z-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle on the course of the Julia-Kocienski reaction is discussed. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5632 / 5639

页数：8

共 38 条

[31] Tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates and a synthetic approach to Cbz-Gly-Ψ[(Z)-CF=C]-Gly dipeptide isostere [J].