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Asymmetric Synthesis of β2-Aryl Amino Acids through Pd-Catalyzed Enantiospecific and Regioselective Ring-Opening Suzuki–Miyaura Arylation of Aziridine-2-carboxylates |
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| Authors: | Prof Dr Youhei Takeda Tetsuya Matsuno Dr Akhilesh K Sharma Prof Dr W M C Sameera Prof Dr Satoshi Minakata |
| Institution: | 1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871 Japan;2. Fukui Institute for Fundamental Chemistry, Kyoto University, Takano-Nishishiraki-cho 34-4, Sakyo-ku, Kyoto, 606-8103 Japan;3. Institute of Low Temperature Science, Hokkaido University, Kita-ku, North 19 West 8, Sapporo, Hokkaido, 060-0819 Japan |
| Abstract: | A Pd-catalyzed enantiospecific and regioselective ring-opening Suzuki–Miyaura arylation of aziridine-2-carboxylates was developed. The cross-coupling allows for the asymmetric preparation of enantioenriched β2-aryl amino acids, starting from commercially available enantiopure d - and l -serine esters. The mechanism and selectivity of the reaction was rationalized based on computational models. |
| Keywords: | amino acids asymmetric synthesis cross-coupling nitrogen heterocycles regioselectivity |