Chemo-, regio-, and stereoselective hydroboration of conjugated enyne alcohol/amine: facile synthesis of Z,Z-/Z,E-1,3-dien-1/2-ylboronic ester bearing hydroxyl/amino group

被引：11

作者：

Xu, Hua-Dong ^{[1
]}

Wu, Hao ^{[1
]}

Jiang, Chun ^{[1
]}

Chen, Peng ^{[1
]}

Shen, Mei-Hua ^{[1
]}

机构：

[1] Changzhou Univ, Sch Pharmaceut Engn & Life Sci, Changzhou 213164, Jiangsu, Peoples R China

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 26期

关键词：

1,3-Enyne; Hydroboration; Dienyl boronic ester; Borylcopper; Bis(pinacolato)diboron; CATALYZED BORYLATION; INTERNAL ALKYNES; COPPER; BIS(PINACOLATO)DIBORON; ADDITIONS;

D O I：

10.1016/j.tetlet.2016.05.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydroboration of conjugated enyne alcohol/amine is studied by using copper salts and bis(pinacolato)diboron as pre-catalysts and boron source respectively. It is suggested that the chemo-selectivity is derived from a combined electronic influence of the heteroatoms on the substrate and the ligand on the transition metal. The regioselectivity is probably dominated mainly by electronic effect of the alkyne substituent. This study resulted in a highly selective protocol to access Z,Z-/Z,E-1,3-dien-1/2-ylboronic ester bearing hydroxyl/amino group. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2915 / 2918

页数：4