Studies on Cu-catalyzed asymmetric alkynylation of tetrahydroisoquinoline derivatives

被引：145

作者：

Li, ZP ^{[1
]}

MacLeod, PD ^{[1
]}

Li, CJ ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 04期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

D O I：

10.1016/j.tetasy.2006.02.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantioselective C-C bond formations between the sp(3) C-H bond of prochiral CH2 and terminal alkynes via the cross-dehydrogenative coupling (CDC) reaction were studied. Efficient asymmetric syntheses of alkynyl tetrahydroisoquinoline derivatives were achieved by using a catalytic amount of CuOTf together with PyBox chiral ligand. When dihydroisocluinolinium salts were used as electrophiles, the combination of CuBr/QUINAP provided the best results for asymmetric syntheses of alkynyl tetrahydroisoquinoline derivatives. The factors influencing the enantioselectivity were studied. (c) 2006 Elsevier Ltd All rights reserved.

引用

页码：590 / 597

页数：8

共 46 条

[1] A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates [J].