Stereocontrolled construction of the dihydrothiopyrano[2,3-b]indole skeleton via an organocatalyzed asymmetric cascade sulfa-Michael-aldol reaction |
| |
| Affiliation: | 1. CEQUINOR (UNLP, CCT-CONICET La Plata), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Blvd. 120 N° 1465, CC 962, La Plata, CP 1900, Argentina;2. Laboratoire de Spectrochimie Infrarouge et Raman, UMR CNRS 8516, Université de Lille 1 Sciences et Technologies, Bât. C5, 59655, Villeneuve d’Ascq Cedex, France;3. Institut des Sciences Moléculaires, UMR CNRS 5255, 351 cours de la Libération, 33405 Talence, Cedex, France;1. Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, PR China;2. Shanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, PR China;3. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, PR China;1. Department of Psychiatry, Mackay Memorial Hospital, Taipei, Taiwan;2. Department of Mathematics, Tamkang University, Taipei, Taiwan;3. Department of Health Care Management, National Taipei University of Nursing and Health Sciences, Taipei, Taiwan;4. Mackay Junior College of Medicine, Nursing, and Management, Taipei, Taiwan |
| |
| Abstract: | We have developed an organocatalyzed asymmetric cascade sulfa-Michael-aldol reaction between 2-mercaptoindole-3-carbaldehydes and enals, which provides efficient access to the stereocontrolled construction of dihydrothiopyrano[2,3-b]indole skeletons. Under the catalysis of chiral diphenylprolinol TMS ether, the reactions ran smoothly to give the corresponding synthetically useful and pharmaceutically valuable dihydrothiopyrano[2,3-b]indoles in high yields and with 64–96% ee. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
