Fast, solvent-free asymmetric alkynylation of prochiral sp3 C-H bonds in a ball mill for the preparation of optically active tetrahydroisoquinoline derivatives

被引：79

作者：

Yu, Jingbo ^{[1
]}

Li, Zhenhua ^{[1
]}

Jia, Kanyan ^{[1
]}

Jiang, Zhijiang ^{[1
]}

Liu, Menglu ^{[1
]}

Su, Weike ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Minist Educ, Key Lab Pharmaceut Engn, Hangzhou 310014, Zhejiang, Peoples R China

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 15期

基金：

浙江省自然科学基金;

关键词：

Asymmetric synthesis; Ball mill; Cross-coupling; C-H activation; Tetrahydroisoquinoline; TARTARIC ACID-ESTER; ENANTIOSELECTIVE ADDITION; TERMINAL ALKYNES; ALDOL REACTION; CONSTRUCTION; DIALKYLZINC; QUINOLINES; ALDEHYDES; ADJACENT;

D O I：

10.1016/j.tetlet.2013.02.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Solvent-free asymmetric cross-dehydrogenative-coupling (CDC) reaction between the sp(3) C-H bond of prochiral CH2 and terminal alkynes was first studied under High-Speed Ball-Milling conditions. A series of optical active 1-alkynyl tetrahydroisoquinoline derivatives were achieved by using recoverable copper balls together with PyBox chiral ligand in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). All coupling products were obtained in good yields at short reaction time with enantiomeric excesses up to 79%. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2006 / 2009

页数：4

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