Journal
TETRAHEDRON LETTERS
Volume 54, Issue 15, Pages 2006-2009Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.02.007
Keywords
Asymmetric synthesis; Ball mill; Cross-coupling; C-H activation; Tetrahydroisoquinoline
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Funding
- Natural Science Foundation of China [20110694]
- Zhejiang Natural Science Foundation [LY12B02020]
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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.
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