Asymmetric Epoxidation of Terminal Olefins with Binaphthyl Strapped Porphyrin Catalysts: (‐( Stacking Interaction and Steric Effects on the Enantioselectivities |
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| Authors: | Qizhi REN Aiqing WANG Shuangyan LIU Xiaojian DING |
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| Institution: | School of Chemistry and Chemical Technology, Shanghai Jiaotong University, Shanghai 200240, China |
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| Abstract: | Two binaphthyl strapped porphyrins with similar chiral auxiliaries 1b and 2b were used as efficient catalysts for asymmetric epoxidation of both styrene derivatives and non‐aromatic olefin substrates. Theoretical calculation of styrene approach to both catalysts has been performed. The subtle difference of the chiral cavities between two porphyrins has been analyzed by 1H NMR. The π‐π stacking interaction between aromatic substrates and catalysts might be one factor for the dramatic different enantioselectivities. Besides, the steric effect of the binaphthyl handle of 1b and 2b also causes the high ee values for non‐aromatic olefin epoxidations. |
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| Keywords: | asymmetric epoxidation chiral porphyrin π‐π stacking interaction enantioselectivity |
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