Studies on Cu-catalyzed asymmetric alkynylation of tetrahydroisoquinoline derivatives |
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| Institution: | 1. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong;2. Department of Chemistry, Faculty of Science, Kyoto University, Japan;1. Inorganic Materials and Catalysis Division, CSIR-Central Salt and Marine Chemicals Research Institute (CSIR-CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar, 364002 Gujarat, India;2. Academy of Scientific and Innovative Research (AcSIR), CSIR-CSMCRI, Bhavnagar, 364002 Gujarat, India;1. Hunan Key Laboratory of Traditional Chinese Veterinary Medicine, Hunan Agricultural University, Changsha, Hunan 410128, China;2. Guilin Layn Natural Ingredients Corporation, Guilin, Guangxi 541199, China;1. Department of Pharmaceutical Analysis, School of Pharmacy, Shandong University of Traditional Chinese Medicine, Ji''nan 250355, China;2. College of Animal Science and Veterinary Medicine, Shandong Agricultural University, Taian 271018, China;3. School of Chemistry and Chemical Engineering, Shandong University, Ji''nan 250100, China;4. State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China |
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| Abstract: | Enantioselective C–C bond formations between the sp3 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 dihydroisoquinolinium 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. |
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