We recently reported the Competing Enantioselective Conversion (CEC) method for determining absolute configuration.1-3 The CEC method for secondary alcohols utilizes the enantioselective acyl-transfer catalyst HBTM. A kinetic analysis of the HBTM-mediated esterification of enantioenriched secondary alcohols is presented herein. In particular, the order of the enantioenriched alcohol, the catalyst, the anhydride, and the base were investigated. In addition to this initial work, a series of enantioenriched benzyl alcohol analogs were tested separately in the esterification using each enantiomer of HBTM. A Hammett plot is reported based on these results. The culmination of these studies provides evidence for the reaction mechanism and the transition state where the HBTM catalyst is involved.1 Wagner, A. J.; David, J. G.; Rychnovsky, S. D. Org. Lett. 2011  , 13, 4470�4473.2 Miller, S. M.; Samame, R. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 2012  , 134, 20318�20321.3 Perry, M. A.; Trinidad, J. V.; Rychnovsky, S. D. Org. Lett. 2013  , 15, 472�475.

Kinetic analysis of the HBTM-mediated esterification of enantioenriched secondary alcohols

246th National Meeting (2013)

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