Ralf Haiges - Difluoro(sulfinato)methylation of N-sulfinyl imines facilitated by 2-pyridyl sulfone: Stereoselective synthesis of difluorinated β-amino sulfonic acids and peptidosulfonamides.

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  Publication Details (including relevant citation   information): Prakash, G. K. Surya, Ni, Chuanfa, Wang,   Fang, Zhang, Zhe, Haiges, Ralf, Olah, George A., Angew.   Chem., Int. Ed., 2013, 52 (41), pp   10835-10839

  Abstract: We have reported a highly   stereoselective synthesis of chiral optically active   α,α-difluoro-β-amino sulfinic and sulfonic acids by   fluoroalkylation of chiral imines using 2-PyS02CF2H as a masked   difluoro(sulfinato)methylation reagent. The transformation was   found to be fairly feasible and easy-to-handle. The difluorinated   β-amino sulfinates are expected to be suitable for constructing   difluorinated peptidosulfonamides. The difluorinated β-amino   sulfonic acids represent a novel class of functionalized   fluoroalkyl sulfonic acids. The preliminary conformational study   of (I) and its nonfluorinated analog demonstrated their   essentially different behavior, which can be of immense interest   in life and materials sciences. [on SciFinder(R)]

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