Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with organoboronic acids

Mark Lautens; Chris Dockendorff; Keith Fagnou; Adrianna Malicki

doi:10.1021/ol0256062

Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with organoboronic acids

Org Lett. 2002 Apr 18;4(8):1311-4. doi: 10.1021/ol0256062.

Authors

Mark Lautens¹, Chris Dockendorff, Keith Fagnou, Adrianna Malicki

Affiliation

¹ Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5H 3H6. [email protected]

PMID: 11950350
DOI: 10.1021/ol0256062

Abstract

The first rhodium(I)-catalyzed asymmetric addition of organoboronic acids to oxabicyclic alkenes is reported. This asymmetric ring-opening (ARO) reaction can proceed in high yield under very mild conditions with electronically diverse organoboronic acids, in a highly diastereoselective and enantioselective manner. [structure: see text]