Asymmetric Michael addition reactions of chiral Ni(II)-complex of glycine with (N-trans-enoyl)oxazolidines: improved reactivity and stereochemical outcome |
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| Affiliation: | 1. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran;2. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran;3. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran;4. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran;1. Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, Hunan, China;2. School of Chemistry and Chemical Engineering, Central South University, Changsha 410083, Hunan, China;1. Molecular Structure Analysis, German Cancer Research Center (DKFZ), Im Neuenheimer Feld 280, D-69009 Heidelberg, Germany;2. NMR Research Centre, Solid State and Structural Chemistry Unit, Indian Institute of Science, IN-560012 Bangalore, India;1. National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;2. University of Chinese Academy of Sciences, Beijing 100049, China;1. Department of Pharmaceutical Engineering, Medical College, Guangxi University, Nanning 530004, China;2. School of Chemistry & Chemical Engineering, Guangxi University, Nanning 530004, China |
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| Abstract: | Application of the (N-trans-enoyl)oxazolidines as Michael acceptors in the kinetically controlled additions with a Ni(II)-complex of the chiral Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone 1 was shown to be synthetically advantageous over the alkyl enoylates, allowing for remarkable improvement in reactivity and, in most cases, diastereoselectivity of the reactions. While the stereochemical outcome of the Michael additions of the aliphatic (N-trans-enoyl)oxazolidines with complex 1 depended on the steric bulk of the alkyl group on the starting oxazolidines, the diastereoselectivity of the aromatic (N-trans-enoyl)oxazolidines reactions was found to be controlled by the electronic properties of the aryl ring. In particular, the additions of complex 1 with (N-cinnamoyl)oxazolidines, bearing electron-withdrawing substituents on the phenyl ring, afforded the (2S,3R)-configured products with synthetically useful selectivity and in quantitative chemical yield, thus allowing an efficient access to sterically constrained β-substituted pyroglutamic acids and related compounds. |
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