N-Fluoro-(3,5-di-tert-butyl-4-methoxy)benzenesulfonimide (NFBSI): A sterically demanding electrophilic fluorinating reagent for enantioselective fluorination

N-Fluoro-(3,5-di-tert-butyl-4-methoxy)benzenesulfonimide (NFBSI): A sterically demanding electrophilic fluorinating reagent for enantioselective fluorination
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DOI:
10.1016/j.jfluchem.2011.01.005
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发表时间:
2011-03
影响因子:
1.9
通讯作者:
H. Yasui;Takeshi Yamamoto;Takehisa Ishimaru;T. Fukuzumi;Etsuko Tokunaga;Kakehi Akikazu;M. Shiro
H. Yasui;Takeshi Yamamoto;Takehisa Ishimaru;T. Fukuzumi;Etsuko Tokunaga;Kakehi Akikazu;M. Shiro
中科院分区:
化学4区
文献类型:
--
作者:
H. Yasui;Takeshi Yamamoto;Takehisa Ishimaru;T. Fukuzumi;Etsuko Tokunaga;Kakehi Akikazu;M. Shiro

文献摘要

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我们在这里公开了一种新型的亲电氟化试剂,N-氟-(3,5-二叔丁基-4-甲氧基)苯磺酰亚胺(NFBSI),作为流行的氟化试剂N-氟苯磺酰亚胺(NFSI)的空间要求类似物。与使用NFSI相比,NFBSI对于金鸡纳碱催化的硅烯醇醚的对映选择性缩合提高了产物的对映选择性多达18%。
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.