Highly enantioselective Mannich reactions of imines with tert-butyl acetoacetate catalyzed by squaramide organocatalyst |
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| Institution: | 1. Department of Chemistry, Karnatak University, Pavate Nagar, Dharwad 580 003, Karnataka, India;2. Centre for Nano and Material Sciences, Jain University, Jain Global Campus, Bangalore 562 112, Karnataka, India;3. Department of Chemistry, Education College, Salahaddin University, Erbil, Iraq;1. Department of Chemistry, Faculty of Science, University of Kurdistan, PO Box 416, Sanandaj, Iran;2. Department of Chemistry, Sanandaj Branch, Islamic Azad University, PO Box 720, Sanandaj, Iran;3. Kurdistan University of Medical Sciences, PO Box 66177-13446, Sanandaj, Iran;4. Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran;1. Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India;2. X-ray Diffraction Laboratory, Department of Chemistry, Texas A&M University, College Station, Texas, TX 77842, USA;1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 420088 Kazan, Russian Federation;2. A. M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, 420008 Kazan, Russian Federation |
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| Abstract: | Highly enantioselective Mannich reactions of imines bearing a benzothiazole moiety with tert-butyl acetoacetate, catalyzed by a cinchona-based squaramide organocatalyst have been developed. The corresponding benzothiazole β-keto ester derivatives were obtained in high yields (up to 99%) and with excellent enantioselectivities (up to 98% ee). |
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