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

Wang, Xianliang; Rissanen, Kari; Bolm, Carsten

doi:10.1021/acs.orglett.3c00415

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Wang, X., Rissanen, K., & Bolm, C. (2023). A One-Pot Domino Reaction Providing Fluorinated 5,6-Dihydro-1,2-thiazine 1-Oxides from Sulfoximines and 1-Trifluoromethylstyrenes. Organic Letters, 25(9), 1569-1572. https://doi.org/10.1021/acs.orglett.3c00415

Julkaistu sarjassa

Organic Letters

Tekijät

Wang, Xianliang |

Rissanen, Kari |

Bolm, Carsten

Päivämäärä

2023

Oppiaine

Orgaaninen kemia Organic Chemistry

Tekijänoikeudet

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.

Julkaisija

American Chemical Society (ACS)

ISSN Hae Julkaisufoorumista

1523-7060

Lisätietoja rahoituksesta

The authors are grateful to the China Scholarship Council (CSC) for a predoctoral fellowship for X.W., and the authors acknowledge the Alexander von Humboldt Foundation for support of K.R. (AvH research award).

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