1200799-49-0Relevant academic research and scientific papers
Iron-Catalyzed Acylative Dealkylation of N-Alkylsulfoximines
Lamers, Philip,Priebbenow, Daniel L.,Bolm, Carsten
, p. 5594 - 5602 (2015/09/01)
As a result of our recent investigations into the N-functionalization of sulfoximines, an iron-catalyzed dealkylative acylation of N-alkylsulfoximines has been developed. This process involves a Polonovski-type dealkylation of an N-alkylated sulfoximine to afford a reactive intermediate that is trapped in the presence of a suitable aldehyde or anhydride to afford N-acyl- and N-aroylsulfoximine derivatives in one pot. Subsequent cleavage of the acyl or aroyl group under acidic conditions generates a synthetically valuable NH-sulfoximine. The dealkylation of N-alkylsulfoximines has been developed utilizing TBHP as oxidant and a catalytic amount of iron chloride to furnish a range of N-acyl- and N-aroylsulfoximines. This method facilitates the use of N-alkyl protecting groups that provide very stable N-protected sulfoximine derivatives that can be readily modified at sites other than the nitrogen atom.
Sulfoximines: A reusable directing group for chemo-and regioselective ortho C-H oxidation of arenes
Yadav, M. Ramu,Rit, Raja K.,Sahoo, Akhila K.
, p. 5541 - 5545 (2012/06/01)
Sulfoximines direct: A new protocol for the chemo-and regioselective ortho C-H acetoxylation of arenes in N-benzoylated sulfoximines is reported. The sulfoximine directing group is easily detached from the C-H oxidation product through acid-promoted hydrolysis, isolated, and reused (see scheme). The meta-substituted phenols are synthesized following this strategy and the stereointegrity of the sulfoximine is preserved in this transformation. C(sp3)-H acetoxylation of the methyl group is also demonstrated.
