Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids from a new chiral glycine equivalent with 3,6-dihydro-2H-1,4-oxazin-2-one structure |
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| Institution: | 1. Departamento de Quı́mica Orgánica, Universidad de Alicante, Apartado 99, 03080 Alicante, Spain;2. Departamento de Quı́mica Inorgánica, Instituto de Ciencias de los Materiales de Aragón, Facultad de Ciencias, Universidad de Zaragoza-CSIC, 50009, Zaragoza, Spain;1. Medicinal Chemistry Research Laboratories, R&D Division, Daiichi Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan;2. Specialty Medicine Research Laboratories I, R&D Division, Daiichi Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan;3. Biomarker & Translational Research Department, R&D Division, Daiichi Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan;4. Pharmacovigilance Department, R&D Division, Daiichi Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan;5. Drug Metabolism & Pharmacokinetics Research Laboratories, R&D Division, Daiichi Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan;1. Department of Materials Science and Engineering, Yonsei University, Seoul, 03722, Republic of Korea;2. Center for Hydrogen Fuel Cell Research, Korea Institute of Science and Technology, 39-1 Hawolgok-Dong, Seongbuk-gu, Seoul, 136-791, Republic of Korea;1. Department of Chemistry & Biochemistry, Miami University, Oxford, OH, 45056, USA;2. Elmer O. Schlemper X-Ray Diffraction Center, University of Missouri-Columbia, Columbia, MO 65211, USA |
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| Abstract: | Condensation of the new chiral glycine equivalent 10 with aldehydes at room temperature in the presence of K2CO3 under solid–liquid phase-transfer-catalysed conditions afforded stereoselectively new chiral (Z)-α,β-didehydroamino acid (DDAA) derivatives with oxazinone structure 14. These systems have been used in diastereoselective cyclopropanation reactions for the synthesis of enantiomerically pure 1-aminocyclopropanecarboxylic acids (ACCs) such as (−)-allo-norcoronamic and (−)-allo-coronamic acids. |
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