Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of α-Amino Acids

…, JR Hummel, RG Bergman, JA Ellman

Index: Lian, Yajing; Hummel, Joshua R.; Bergman, Robert G.; Ellman, Jonathan A. Journal of the American Chemical Society, 2013 , vol. 135, # 34 p. 12548 - 12551

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Abstract

A high yielding and practical two-step synthesis of enantiomerically pure perfluorobutanesulfinamide from Senanayake's 2-aminoindanol-derived sulfinyl transfer reagent was developed and carried out on a multigram scale. Straightforward condensation of this sulfinamide with ethyl glyoxylate provided the N-perfluorobutanesulfinyl imino ester. The utility of this activated N-sulfinyl imino ester was demonstrated for reactions that gave ...