Stereoselective synthesis of (R)- and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acids, -carboxylates and -carboxamides |
| |
| Institution: | 1. Department of Pharmacology, Kahramanmaras Sutcu Imam University, Faculty of Medicine, Kahramanmaraş, Turkey;2. Department of Physical Medicine and Rehabilitation, Kahramanmaras Sutcu Imam University, Faculty of Medicine, Kahramanmaraş, Turkey;3. Department of Biophysics, Kahramanmaras Sutcu Imam University, Faculty of Medicine, Kahramanmaraş, Turkey;1. Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy;2. Dipartimento di Biotecnologie, Chimica e Farmacia, Università di Siena, Via A. Moro, 53100 Siena, Italy;1. Program in Chemical Biology, Sloan Kettering Institute, New York, NY 10065, USA;2. Department of Medicine, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA;1. Famur PLC, 51 Armii Krajowej St., 40-698 Katowice, Poland;2. The Silesian University of Technology, the Faculty of Mining and Geology, 2 Akademicka St., 44-100 Gliwice, Poland |
| |
| Abstract: | (R)-Monomethyl 2-methyl-2-(2-nitrophenoxy)malonates obtained by PLE catalyzed hydrolysis of the corresponding dimethyl malonates undergo solvent-dependent enantioselective cyclization to afford (R)-methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acids, respectively. These compounds are easily converted to enantiomerically and diastereomerically pure carboxamides, which are used as peptidomimetic building blocks. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
