A One-Pot Domino Reaction Providing Fluorinated 5,6-Dihydro-1,2-thiazine 1-Oxides from Sulfoximines and 1-Trifluoromethylstyrenes
Xianliang Wang, Kari Rissanen, Carsten Bolm
Abstract
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 (S N 2′), (2) hydrolysis, and (3) intramolecular nucleophilic vinylic substitution (S N V). The products can further be modified by defluorination. The molecular structure of the resulting product was confirmed by X-ray crystallographic analysis.
Topics & Concepts
ChemistrySN2 reactionThiazineIntramolecular forceAllylic rearrangementNucleophilic substitutionNucleophileDominoHydrolysisMedicinal chemistrySubstitution (logic)Combinatorial chemistryOrganic chemistryCatalysisProgramming languageComputer scienceSynthesis and Catalytic ReactionsFluorine in Organic ChemistrySulfur-Based Synthesis Techniques