Dynamic kinetic resolution via asymmetric conjugate reduction: enantio- and diastereoselective synthesis of 2,4-dialkyl cyclopentanones |
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Authors: | Jurkauskas Valdas Buchwald Stephen L |
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Institution: | Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA. |
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Abstract: | Herein, we report the kinetic and the dynamic kinetic resolutions of racemic 3,5-dialkyl-2-cyclopenten-1-ones. Kinetic resolution, with good selectivity factors (25-52), was achieved by conjugate reduction with catalytic CuCl/NaOt-Bu/(S)-p-tol-BINAP and stoichiometric quantities of poly(methylhydrosiloxane) (PMHS). When stoichiometric amounts of NaOt-Bu and t-BuOH were included in the reaction mixture, rapid racemization of the starting material occurred allowing for the dynamic kinetic resolution of the cyclopentenone substrates. In this process, chiral 2,4-dialkylcyclopentanones were isolated with high stereoselectivity (ee > or = 91%, dr > or = 90:10) and in high yield (> or =89%). |
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