title: Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.
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.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Neel
authors.forename: Jörg P
authors.initials: JP
authors.lastname: Hehn
authors.forename: Pascal F
authors.initials: PF
authors.lastname: Tripet
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D002384:Catalysis; D015195:Drug Design; D006860:Hydrogen Bonding; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D010756:Phosphoric Acids; D044005:Tetrahydroisoquinolines; D014230:Triazoles
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