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New chiral nitrones as precursors of α,α-disubstituted amino-acids,according to the SRS principle
Affiliation:1. Department of Bioorganic Chemistry, Chair of Organic Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Krakow, Poland;2. Department of Organic Chemistry, Chair of Organic Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Krakow, Poland;3. Department of Chemistry, Institute of Biology, Pedagogical University, Podchorążych 2, 30-084 Krakow, Poland;4. Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland;5. Department of Pharmaceutical Biochemistry, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Krakow, Poland;1. Apicore Pharmaceuticals Pvt. Ltd, Block No. 252-253, Dhobikuva Village, Padra-Jambusar Highway, Padra Taluka, Vadodara 391 440, India;2. Department of Chemistry, Amet University, 135, East Coast Road, Kanathur, Chennai 603 112, India;3. Department of Chemistry, Faculty of Science, M. S. University of Baroda, Vadodara 390 002, India;1. School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 211116, PR China;2. School of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou 211116, PR China;1. Department of Inorganic and Analytical Chemistry, University of Debrecen, H-4032 Debrecen, Hungary;2. Department of Chemistry and Pharmacy, University of Sassari, Via Vienna 2, I-07100 Sassari, Italy;1. Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India;2. Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
Abstract:The preparation of new enantiopure cyclic nitrones based on the 1-oxy-2,3-dihydro-imidazol-4-one ring is described. The addition of arylmagnesium or alkynylzinc reagents to these nitrones can be achieved with total enantio- and diastereoselectivity, leading to α,α-disubstituted amino-acid precursors.
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