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

TETRAHEDRON LETTERS

卷:54

Article

Yu, Jingbo¹  Li, Zhenhua¹  Jia, Kanyan¹  Jiang, Zhijiang¹  Liu, Menglu¹  Su, Weike¹ 

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

关键词: Asymmetric synthesis;    Ball mill;    Cross-coupling;    C-H activation;    Tetrahydroisoquinoline;   

DOI  :  10.1016/j.tetlet.2013.02.007

来源: Elsevier

【 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.

【 授权许可】

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