Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing
Andrew J Neel1, Jörg P Hehn, Pascal F Tripet
1Department of Chemistry, University of California , Berkeley, California 94720, United States.
Abstract:
This report describes the development of an enantioselective C-N bond-forming reaction to produce 1,2,3,4-tetrahydroisoquinoline-derived cyclic aminals catalyzed by chiral phosphate anions. Central to the success of this goal was the design of a library of 3,3'-triazolyl BINOL-derived phosphoric acids capable of forming attractive hydrogen-bonding interactions with the peptide-like substrate. We envision this work will offer an alternative to the conventional strategy of increasing catalyst steric bulk to improve enantioselectivity with BINOL-derived phosphoric acids.
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