Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions

被引：17

作者：

Stockhammer, Lotte ^{[1
]}

Weinzierl, David ^{[1
]}

Boegl, Thomas ^{[2
]}

Waser, Mario ^{[1
]}

机构：

[1] Johannes Kepler Univ Linz, Inst Organ Chem, A-4040 Linz, Austria

[2] Johannes Kepler Univ Linz, Inst Analyt Chem, A-4040 Linz, Austria

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 15期

基金：

奥地利科学基金会;

关键词：

CATALYSIS; HETEROFUNCTIONALIZATION; FLUORINATION; KETENES; DERIVATIVES;

D O I：

10.1021/acs.orglett.1c02256

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric alpha-chlorination of activated aryl acetic acid esters can be carried out with high levels of enantioselectivities utilizing commercially available isothiourea catalysts under base-free conditions. The reaction, which proceeds via the in situ formation of chiral C1 ammonium enolates, is best carried out under cryogenic conditions combined with a direct trapping of the activated alpha-chlorinated ester derivative to prevent epimerization, thus allowing for enantioselectivities of up to e.r. 99:1.

引用

页码：6143 / 6147

页数：5

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