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A short enantioselective total synthesis of (R)- and (S)-pipecolic acid
Affiliation:1. Department of Chemistry, College of Life Sciences and Environment, Shanghai Normal University, 100 Guilin Road, Shanghai 200234, China;2. The Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;1. RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan;2. Department of Chemistry, The Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama, Tokyo 152-8551, Japan;3. Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan;1. College of Chemistry and Molecular Engineering, Zhengzhou University, 100 Kexue Road, Zhengzhou 450001, PR China;2. State Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, PR China
Abstract:A convenient and practical total synthesis of (R)- and (S)-pipecolic acid has been achieved by utilizing chiral cis-aziridine-2-carboxylate as the common synthetic precursor. The synthesis involves regioselective reductive cleavage of the aziridine ring and Wittig olefination as key reactions.
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