Professional Education

  • Doctor of Philosophy, Harvard University (2016)

Stanford Advisors

Contact

  • sbanik@stanford.edu
    University - Scholar Department: Chemistry Position: Postdoctoral Scholar

All Publications

  • Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis Science Banik, S. M., Levina, A., Hyde, A. M., Jacobsen, E. N. 2017; 358: 761-764
  • Catalytic 1,3-Difunctionalization via Oxidative C–C Bond Activation Journal of the American Chemical Society Banik, S. M., Mennie, K. M., Jacobsen, E. N. 2017; 139 (27): 9152-9155
  • Catalytic, asymmetric difluorination of alkenes to generate difluoromethylated stereocenters Science Banik, S. M., Medley, J. W., Jacobsen, E. N. 2016; 353 (6294): 51-54

    View details for DOI 10.1126/science.aaf8078

  • Catalytic, Diastereoselective 1,2-Difluorination of Alkenes Journal of the American Chemical Society Banik, S. M., Medley, J. W., Jacobsen, E. N. 2016; 138 (15): 5000-5003
  • Chemoselective pd-catalyzed oxidation of polyols: synthetic scope and mechanistic studies. Journal of the American Chemical Society Chung, K., Banik, S. M., De Crisci, A. G., Pearson, D. M., Blake, T. R., Olsson, J. V., Ingram, A. J., Zare, R. N., Waymouth, R. M. 2013; 135 (20): 7593-7602

    Abstract

    The regio- and chemoselective oxidation of unprotected vicinal polyols with [(neocuproine)Pd(OAc)]2(OTf)2 (1) (neocuproine = 2,9-dimethyl-1,10-phenanthroline) occurs readily under mild reaction conditions to generate α-hydroxy ketones. The oxidation of vicinal diols is both faster and more selective than the oxidation of primary and secondary alcohols; vicinal 1,2-diols are oxidized selectively to hydroxy ketones, whereas primary alcohols are oxidized in preference to secondary alcohols. Oxidative lactonization of 1,5-diols yields cyclic lactones. Catalyst loadings as low as 0.12 mol % in oxidation reactions on a 10 g scale can be used. The exquisite selectivity of this catalyst system is evident in the chemoselective and stereospecific oxidation of the polyol (S,S)-1,2,3,4-tetrahydroxybutane [(S,S)-threitol] to (S)-erythrulose. Mechanistic, kinetic, and theoretical studies revealed that the rate laws for the oxidation of primary and secondary alcohols differ from those of diols. Density functional theory calculations support the conclusion that β-hydride elimination to give hydroxy ketones is product-determining for the oxidation of vicinal diols, whereas for primary and secondary alcohols, pre-equilibria favoring primary alkoxides are product-determining. In situ desorption electrospray ionization mass spectrometry (DESI-MS) revealed several key intermediates in the proposed catalytic cycle.

    View details for DOI 10.1021/ja4008694

    View details for PubMedID 23659308