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
收藏
页码：2006 / 2009
页数：4
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