One-Pot O2-Oxidation and the Horner-Wadsworth-Emmons Reaction of Primary Alcohols for the Synthesis of (Z)-α,β-Unsaturated Esters

被引：2

作者：

Ando, Kaori ^{[1
]}

Takaba, Chika ^{[1
]}

Kodama, Masahiro ^{[1
]}

机构：

[1] Gifu Univ, Fac Engn, Dept Chem & Biomol Sci, Gifu, 5011193, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 15期

关键词：

OXIDATION-WITTIG REACTION; Z-SELECTIVE SYNTHESIS; Z-UNSATURATED ESTERS; C BOND FORMATION; AEROBIC OXIDATION; ETHYL (DIARYLPHOSPHONO)ACETATES; ALPHA; BETA-UNSATURATED ESTERS; STEREOSELECTIVE-SYNTHESIS; MANGANESE-DIOXIDE; CONVENIENT;

D O I：

10.1021/acs.joc.2c00763

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed one-pot oxidation/olefination procedures of primary alcohols giving Z-alpha,beta-unsaturated esters 3. TEMPO-(CuCl or CuBr2)-(2,2'-bipyridine) (1:1:1) catalyzed O-2 oxidation of primary alcohols in the presence of Z-selective Horner-Wadsworth-Emmons reagent lb and K3PO4 or NaH gave 3 with Z/E = 84:16 to 96:4 in high yields. A stepwise reaction was also developed. After TEMPO-CuBr2-(2,2'-bipyridine)-K3PO4 (1:1:1:1) catalyzed O-2 oxidation of alcohols in MeCN, the resulting mixture was treated with a THF solution of lb and t-BuOK at -78 degrees C to 0 degrees C, giving 3 with higher selectivity (Z/E = 91:9 to 99:1).

引用

页码：9723 / 9728

页数：6

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