Stereocontrolled metalloenamine alkylations: application to the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines |
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| Institution: | 1. Immunotherapy Convergence Research Center, Korea Research Institute of Bioscience & Biotechnology (KRIBB), Daejeon 34141, Republic of Korea;2. Bio & Drug Discovery Division, Center for Drug Discovery Technology, Korea Research Institute of Chemical Technology (KRICT), Daejeon 305-600, Republic of Korea;3. Department of Internal Medicine, Chungnam National University School of Medicine, 266 Munhwa-ro, Jung-gu, Daejeon 35015, Republic of Korea;4. Chungnam National University School of Medicine, Rm 129, 266 Munhwaro, Daejeon 301-747, Republic of Korea;1. College of Electronic Information and Optical Engineering, Nankai University, Tianjin, 300350, China;2. Tianjin Key Laboratory of Optoelectronic Sensor and Sensing Network Technology, Tianjin, 300350, China;3. Engineering Research Center of Thin Film Optoelectronics Technology, Ministry of Education, Nankai University, Tianjin, 300350, China;1. Department of Microbiology and Immunology, Life Sciences Institute, The University of British Columbia, Vancouver, Canada;2. Renewable Resources and Enabling Sciences Center, National Renewable Energy Laboratory, Golden, Colorado, USA;3. Center for Bioenergy Innovation, Oak Ridge National Laboratory, Oak Ridge Tennessee, USA;4. BioProducts Institute, The University of British Columbia, Vancouver, Canada;1. Laboratory of Nuclear Energy Chemistry, Institute of High Energy Physics, Chinese Academy of Sciences, Beijing 100049, PR China;2. College of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001, PR China;3. Engineering Laboratory of Advanced Energy Materials, Institute of Industrial Technology, Chinese Academy of Sciences, Ningbo 315201, PR China;1. Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India;2. School of Chemistry, University of Hyderabad, Hyderabad 500 046, India;1. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang, 330013, PR China;2. Department of Ecology and Environment, Yuzhang Normal University, Nanchang, 330103, PR China |
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| Abstract: | A procedure for the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines is described. The key step in the synthetic route is a stereocontrolled metalloenamine alkylation using (R)-(+)-phenylglycinol methyl ether as the chiral auxiliary. Subsequent N-methylation, hydrogenolysis and cyclization afforded the target heterocycles with enantiomeric excesses higher than 99%. |
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