Chiral thiophene dioxides and thiophene S,N-ylides as dienes for asymmetric diels-aldlr application |
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| Institution: | 1. Laboratory of Immunology and Inflammation, Research Center of Basic Medical Science, Tianjin Medical University, Tianjin, China;2. Department of Immunology, Basic Medical College, Tianjin Medical University, Tianjin, China;3. Key Laboratory of Immune Microenvironment and Diseases of Educational Ministry of China, Tianjin Medical University, Tianjin, China;4. Department of Immunology, Basic Medical College, Weifang Medical University, Weifang, China;5. Department of Pharmacology, School of Basic Medical Sciences, Tianjin Medical University, Tianjin, China;6. School of Medical Imaging, Tianjin Medical University, Tianjin 300070, China;7. Department of Gastroenterology, Peking University First Hospital, Beijing, China;8. Department of Genitourinary Oncology, Tianjin Medical University Cancer Hospital, Key Laboratory of Cancer Prevention and Therapy, Tianjin, China;9. Storr Liver Unit, Westmead Millennium Institute, The Western Clinical School of the University of Sydney, Westmead Hospital, Westmead, NSW 2145, Australia |
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| Abstract: | 2-Menthyltrihalothiophene S,S-dioxides are efficient asymmetric dienes in Diels-Alder reactions with dienophiles to give regio- and stereoisomerically pure adducts. Thus styrene, allyl alcohol, methyl acrylate and acrylamide give solely one adduct while flat dienophiles such as indene and acenaphthylene give two diastereomers. Analogous 1- and 3- chirally substituted thiophenes are of little value in generating pure single adducts. Further transformations of the above adducts into useful enantiomerically pure compounds is briefly discussed. |
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