A One-Pot Domino Reaction Providing Fluorinated 5,6-Dihydro-1,2-thiazine 1-Oxides from Sulfoximines and 1-Trifluoromethylstyrenes

被引：12

作者：

Bolm, Carsten ^{[1
]}

Wang, Xianliang ^{[1
]}

Rissanen, Kari ^{[2
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

[2] Univ Jyvaskyla, Dept Chem, FI-40014 Jyvaskyla, Finland

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 09期

关键词：

F BOND ACTIVATION; 3-DIMENSIONAL HETEROCYCLES; FUNCTIONALIZATION; SUBSTITUTION; ANNULATION; ACIDS;

D O I：

10.1021/acs.orglett.3c00415

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Trifluoroacetylated (N-TFA) sulfoximines react with 1-trifluoromethylstyrenes in a one-pot domino reaction to give fluorinated 5,6-dihydro-1,2-thiazine 1-oxides in good to high yields. The process involves three sequential reaction steps that can be characterized as (1) nucleophilic allylic substitution (SN2 '), (2) hydrolysis, and (3) intramolecular nucleophilic vinylic substitution (SNV). The products can further be modified by defluorination. The molecular structure of the resulting product was confirmed by X-ray crystallographic analysis.

引用

页码：1569 / 1572

页数：4

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