Enantioselective Desymmetrization of Curcumins with 3-Olefinic Oxindoles for the Synthesis of Spirocyclohexanoneoxindoles |
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| Authors: | Dr. Chenikkayala Siva Sankara Dr. Shweta Bhagat Dr. Ajeet Chandra Prof. Dr. Irishi N. N. Namboothiri |
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| Affiliation: | Department of Chemistry, Indian Institute of Technology Bombay, 400076 Mumbai, Maharashtra, India |
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| Abstract: | An enantioselective desymmetrization of curcumins with 3-olefinic oxindoles involving a cascade double-Michael addition strategy provides direct access to spirocyclohexanone-oxindoles with complete regio- and diastereoselectivities and excellent enantioselectivities, besides good to excellent yields. The products possess three contiguous chiral centers and multiple reactive functionalities. The observed selectivities were rationalized by transitions state energy calculations at B3LYP//6-31g(d) level of DFT. |
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| Keywords: | synthetic methods curcumin DFT calculations enantioselective desymmetrization spiro-oxindoles |
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