Silicon-Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism

被引：93

作者：

Liang, Dong-Dong ^{[1
]}

Streefkerk, Dieuwertje E. ^{[1
]}

Jordaan, Daan ^{[1
]}

Wagemakers, Jorden ^{[1
]}

Baggerman, Jacob ^{[1
]}

Zuilhof, Han ^{[1
,2
,3
]}

机构：

[1] Wageningen Univ, Lab Organ Chem, Stippeneng 4, NL-6708 WE Wageningen, Netherlands

[2] Tianjin Univ, Sch Pharmaceut Sci & Technol, 92 Weijin Rd, Tianjin, Peoples R China

[3] King Abdulaziz Univ, Fac Engn, Dept Chem & Mat Engn, Jeddah, Saudi Arabia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 19期

基金：

美国国家科学基金会;

关键词：

enantioselectivity; kinetics; reaction mechanisms; SuFEx; THIOLATE-DISULFIDE EXCHANGE; CLICK CHEMISTRY; NUCLEOPHILIC-SUBSTITUTION; ADDITION-ELIMINATION; SILYL ETHERS; BIOCONJUGATION; SULFOXIMINES; POLYSULFATES; CONVERSION; SECONDARY;

D O I：

10.1002/anie.201915519

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

SuFEx reactions, in which an S-F moiety reacts with a silyl-protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high-yielding, "Si-free" and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products.

引用

页码：7494 / 7500

页数：7

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