Late-stage diversification of chiral N-heterocyclic-carbene precatalysts for enantioselective homoenolate additions.
A library of chiral triazolium salts has been prepared by late-state diversification of a triazolium amine salt. By utilizing a primary amine as a functional handle, a single triazolium salt can be transformed into a variety of chiral N-heterocyclic carbene precatalysts. This approach makes the preparation of chiral N-heterocyclic carbenes possible by a single-step modification of a triazolium salt, rather than the usual need for multistep organic synthesis and challenging heterocycle formation for each member of a catalyst library. We have screened these catalysts for control of diastereo- and enantioselectivity in a γ-lactam-forming reaction between α,β-unsaturated aldehydes and cyclic ketimines.
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA.
Pinguan
P
Zheng
Chenaimwoyo A
CA
Gondo
Jeffrey W
JW
Bode
D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry
D006571:Heterocyclic Compounds; D014230:Triazoles; C030011:carbene; D008697:Methane
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