Experimental transition state for the B-chlorodiisopinocampheylborane (DIP-Cl) reduction |
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Authors: | Sean E Stafford |
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Institution: | School of Natural Sciences, University of California, Merced, PO Box 2039, Merced, CA 95344, USA |
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Abstract: | Asymmetric reductions of prochiral ketones are important transformations in the syntheses of natural products, pharmaceuticals, and fine chemicals. B-Chlorodiisopinocampheylborane (DIP-Cl), a stoichiometric reagent that is capable of reducing prochiral aralkyl ketones with high selectivity. Here, we utilize a recently developed 13C kinetic isotope effect (KIE) methodology to probe the symmetry breaking process inherent to this asymmetric reduction. Experimental KIEs and computed transition structures indicate significant roles for non-bonding interaction, specific directed orbital interactions, and hydrogen tunneling in this reaction. |
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