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 4 条

[1] gem-Difluoroolefination of Diaryl Ketones and Enolizable Aldehydes with Difluoromethyl 2-Pyridyl Sulfone: New Insights into the Julia-Kocienski Reaction
Gao, Bing
Zhao, Yanchuan
Hu, Mingyou
Ni, Chuanfa
Hu, Jinbo
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (25) : 7803 - 7810
[2] The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia-Kocienski reaction
Rehman, Mintu
Surendran, Sravya
Siddavatam, Nagendra
Rajendar, Goreti
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (02) : 329 - 333
[3] One-Pot Preparation of (E)-α,β-Unsaturated Aldehydes by a Julia-Kocienski Reaction of 2,2-Dimethoxyethyl PT Sulfone Followed by Acid Hydrolysis
Ando, Kaori
Watanabe, Haruka
Zhu, Xiaoxian
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (09): : 6969 - 6973
[4] Stereoselective Synthesis of Trisubstituted (Z)-Alkenes from Ketones via the Julia-Kocienski Olefination Using 1-Methyl- and 1-tert-Butyl-1H-tetrazol-5-yl Alkyl Sulfones
Ando, Kaori
Takama, Daiki
ORGANIC LETTERS, 2020, 22 (17) : 6907 - 6910

← 1 →