N-Fluoro-(3,5-di-tert-butyl-4-methoxy)benzenesulfonimide (NFBSI): A sterically demanding electrophilic fluorinating reagent for enantioselective fluorination |
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Authors: | Hiroyuki Yasui Takehisa Ishimaru Etsuko Tokunaga Motoo Shiro |
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Institution: | a Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan b Department of Applied Chemistry, Shinshu University, 4-17-1, Wakasato, Nagano 380-8553, Japan c Rigaku Corporation, 3-9-12 Matsubara-cho, Akishima, Tokyo 196-8666, Japan |
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Abstract: | We disclose here a novel electrophilic fluorinating reagent, N-fluoro-(3,5-di-tert-butyl-4-methoxy)benzenesulfonimide (NFBSI) as a sterically demanding analogue of popular fluorinating reagent, N-fluorobenzenesulfonmide (NFSI). NFBSI improves the enantioselectivity of the products as much as 18% for the cinchona alkaloid-catalyzed enantioselective fluorination of silylenol ether compared to the use of NFSI. |
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Keywords: | Electrophilic fluorination Fluorinating reagent Catalytic Enantioselective Synthesis |
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