[2+2] Cycloaddition of chlorosulfonyl isocyanate to allenyl-sugar ethers |
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| Affiliation: | 1. Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland;2. Institute of Physical Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland;1. Department of Chemistry, Manipal Institute of Technology, Manipal University, 576 104, Karnataka, India;2. Department of Radiation Biology & Toxicology, School of Life Sciences, Manipal University, 576 104, Karnataka, India;3. Department of Atomic and Molecular Physics, Manipal University, 576 104, Karnataka, India;1. School of Pharmaceutical Sciences, and Institute of Drug Discovery & Development, Zhengzhou University, 100 Kexue Avenue, Zhengzhou, Henan 450001, China;2. Key Laboratory of Technology of Drug Preparation (Zhengzhou University), Ministry of Education of China, China;3. Key Laboratory of Henan Province for Drug Quality and Evaluation, China;4. Key Laboratory of Targeting Therapy and Diagnosis for Critical Diseases, Henan Province, China;5. Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, China;6. Pharmaceutical Department, The People''s Hospital of Chizhou, 3 Baiya Road, Chizhou, Anhui 247000, China;7. Pharmaceutical Department, Affiliated Hospital of Binzhou Medical College, 661 Yellow River 2nd Road, Binzhou, Shandong 256600, China;8. Department of Pharmacy, Zhengzhou Central Hospital Affiliated to Zhengzhou University, 195 Tongbai Road, Zhengzhou 450053, Henan, China;1. CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, CP C1428EGA, Buenos Aires, Argentina;2. IQUIBICEN-CONICET, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, CP C1428EGA, Buenos Aires, Argentina |
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| Abstract: | ![]()
The direction and magnitude of asymmetric induction in the [2+2] cycloaddition of chlorosulfonyl isocyanate to 3-O-allenyl-α-d-xylofuranoses was investigated. It is shown that gem terminal dimethylallenes react more readily than methyl free congeners. The configuration of adducts was established by X-ray and CD-spectroscopy of alkylidene cephams. A stereochemical model of the transition state for the [2+2] cycloaddition of chlorosulfonyl isocyanate and allenyl ethers is proposed, based on the lowest energy conformation of the cumulene. |
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