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Chiral four-membered cyclic nitrones; asymmetric induction in the (4+2)-cycloaddition reaction of chiral ynamines and nitroalkenes
Institution:1. Wrocław University of Technology, Department of Organic Chemistry, Wybrzeże Wyspiańskiego 27, Wrocław 50-370, Poland;2. Polish Academy of Sciences, Institute of Immunology and Experimental Therapy, Department of Experimental Oncology, Rudolfa Weigla 12, Wrocław 53-114, Poland;1. Department of Applied Chemistry, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan;2. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1, Horinouchi, Hachioji, Tokyo 192-0392, Japan;3. Aix Marseille Université, Ecole Centrale Marseille, CNRS, ISM2 UMR7313, 13397 Cedex 20, Marseille, France;1. School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province 312000, China;2. Zhejiang Zhenyuan Pharmaceutical Co., Ltd, Shaoxing, Zhejiang Province 312000, China;1. School of Chemistry and Chemical Engineering, Shandong University, Jinan, Shandong 250100, China;2. Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, Qinghai 810001, China;3. School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165, China
Abstract:Chiral four-membered cyclic nitrones were synthesized by the asymmetric (4+2)-cycloaddition of nitroalkenes 1 and chiral ynamines 2. The subsequent stereoselective addition of nucleophiles to these nitrones enabled the synthesis of chiral N-hydroxyazetidines.
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