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Regiodivergent Resolution of Unsymmetrical Oxabicyclic Alkenes
R. Webster, C. Böing, M. Lautens*
University of Toronto, Canada
23 March 2009 (online)
The Lautens group reports a rare example of a regiodivergent resolution of bridgehead-substituted oxabenzonorbornene derivatives under rhodium catalysis. From earlier work, these oxabicycles were shown to undergo [Rh(CO)2Cl]2-catalyzed addition of methanol to provide product type A based on complete substrate control. However, when these substrates were treated with a chiral rhodium complex, two regioisomers (type A and B) resulting from Rh insertion into either C-O bond were obtained each in excellent enantioselectivity. Subsequently, various oxabicycles and alcohol- and amine-based nucleophiles could be used under these reaction conditions.