A rhodium IBiox[(-)-menthyl] complex as a highly selective catalyst for the asymmetric hydroarylation of azabicyles: an alternative route to epibatidine

Jason Bexrud; Mark Lautens

doi:10.1021/ol101067d

A rhodium IBiox[(-)-menthyl] complex as a highly selective catalyst for the asymmetric hydroarylation of azabicyles: an alternative route to epibatidine

Org Lett. 2010 Jul 16;12(14):3160-3. doi: 10.1021/ol101067d.

Authors

Jason Bexrud¹, Mark Lautens

Affiliation

¹ Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.

PMID: 20550216
DOI: 10.1021/ol101067d

Abstract

The synthesis and characterization of a new chiral rhodium N-heterocyclic carbene complex, Rh(IBiox[(-)-menthyl](CO)(2)Cl, is reported. In addition, the very high enantioselectivity exhibited by this complex, as a catalyst for the asymmetric hydroarylation of azabicycles, is demonstrated and applied to the synthesis of epibatidine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Catalysis
Organometallic Compounds / chemistry*
Pyridines / chemistry*
Rhodium / chemistry*
Stereoisomerism
Substrate Specificity

Substances

Bridged Bicyclo Compounds, Heterocyclic
Organometallic Compounds
Pyridines
Rhodium
epibatidine