Enatioselective Chalcogeno‐Baylis‐Hillman Reaction of Arylaldehydes with MVK and Acrylates Catalyzed by Chiral Thiepin‐TiCl4 Complex |
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| Authors: | Yan Yin Guofeng Sun Heng Zhang Hong Zhou Fanhong Wu |
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| Institution: | 1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China;2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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| Abstract: | In a rational chiral molecular design of chalcogenides, optically active thiepin with C2‐symmetric chirality was synthesized from commercially available thiophene. Then enatioselective Chalcogeno‐Baylis‐Hillman reactions of arylaldehydes with methyl vinyl ketone (MVK) and acrylates were investigated in the presence of thiepin‐Lewis acid complex. Finally, up to 64% ee was achieved in the presence of 0.2 equiv. of (S)‐thiepin at 20°C. |
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| Keywords: | 3 3′ ‐bithienyls chiral thiepin Chalcogeno‐Baylis‐Hillman reaction chalcogenides TiCl4 |
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