Highly Z-selective synthesis of α,β-unsaturated nitriles using the Horner-Wadsworth-Emmons reaction

被引：20

作者：

Ando, Kaori ^{[1
]}

Okumura, Miho ^{[1
]}

Nagaya, Shigeo ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 15期

关键词：

The HWE reaction; alpha; beta-Unsaturated nitriles; Z-Selective; Stereoselectivity; Aldehydes; STEREOSELECTIVE CARBONYL OLEFINATION; Z-UNSATURATED ESTERS; ETHYL (DIARYLPHOSPHONO)ACETATES; ORGANOSILICON COMPOUNDS; PRACTICAL SYNTHESIS; REAGENTS; ALDEHYDES; STEREOCHEMISTRY; HYDROARYLATION; PHOSPHONATE;

D O I：

10.1016/j.tetlet.2013.02.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new HWE reagent, (o-tBuC(6)H(4)O)(2)P(O)CH2CN (2e), reacts with various types of aldehydes to give Z-alpha,beta-unsaturated nitriles with 86% to >99% Z-selectivity. Especially, the reaction of 2e with bulkier aldehydes, both aromatic and aliphatic, gave the Z-olefins with extremely high selectivity. The combination of t-BuOK and 18-crown-6 (1 equiv) is the base of choice for aromatic aldehydes and t-BuOK is generally the base of choice for aliphatic aldehydes. (C)2013 Elsevier Ltd. All rights reserved.

引用

页码：2026 / 2028

页数：3

共 31 条

[1] Convenient preparations of (diphenylphosphono)acetic and esters and the comparison of the Z-selectivities of their Horner-Wadsworth-Emmons reaction with aldehydes depending on the ester moiety [J].