First synthesis of (1S,2S)- and (1R,2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones |
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| Institution: | 1. North-Caucasian Zonal Research Veterinary Institute, 346493 Novocherkassk, Russian Federation;2. Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, Russian Federation;3. InterBioScreen Ltd., 142432 Chernogolovka, Moscow Region, Russian Federation;4. Don State Agrarian University, 346493 Novocherkassk, Russian Federation;1. Equipe Synthèse Propriétés et Modélisation des Matériaux, Institut de Chimie Moléculaire et des Matériaux d′Orsay, Université Paris-Sud, Université Paris-Saclay, 91405 Orsay, France;2. Laboratoire Léon Brillouin, CEA, CNRS, Université Paris-Saclay, F-91191 Gif sur Yvette, France;3. Institut Nanosciences et Cryogénie (INAC)–Service de Physique Statistique Magnétisme et Supraconductivité (SPMS), CEA and Université Joseph Fourier, F-38000 Grenoble, France;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jagiellonian University, Medical College, Kraków, Poland;2. Department of Pharmacodynamics, Faculty of Pharmacy, Jagiellonian University, Medical College, Kraków, Poland;3. Department of Pharmacobiology, Faculty of Pharmacy, Jagiellonian University, Medical College, Kraków, Poland;4. Università degli Studi di Cagliari, Faculty of Pharmacy and Biology, Cagliari, Italy;1. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India;2. Molecular & Structural Biology Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India;3. Academy of Scientific and Innovative Research, New Delhi, India |
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| Abstract: | An efficient and easy one-pot reaction from readily available racemic 2-substituted cyclobutanones gave, by means of asymmetric Strecker synthesis in the presence of an amine chiral auxiliary, two major aminonitriles with excellent diastereoselectivity. After separation, the major cis-aminonitriles were hydrolysed and hydrogenolysed to lead for the first time to pure non-racemic (+)-1-amino-2-isopropylcyclobutanecarboxylic acid (ACBC) and its antipode. |
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