Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 6, Issue 2, Pages 614-620Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201000617
Keywords
carbenes; asymmetric catalysis; heterocycles; homoenolates; N-heterocyclic carbenes
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Funding
- National Science Foundation [CHE-0449587]
- National Institutes of Health [GM-079339]
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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 gamma-lactam-forming reaction between alpha,beta-unsaturated aldehydes and cyclic ketimines.
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