Iridium-Catalyzed AsymmetricRing-Opening of Azabicyclic Alkenes with Phenols.

The asymmetric ring-opening of azabicyclic alkenes witha variety of phenols is investigated using an iridium catalyst generatedin situ from 2.5 mol % of [Ir(COD)Cl]2and 5.0 mol % of(S)-BINAP, which afforded the corresponding 1,2-trans-phenoxyamino products in excellent yield (up to 92%)with moderate to good enantioselectivities (up to 98% ee). The trans-configuration of the product 4bwas confirmedby X-ray crystallography. [ABSTRACT FROM AUTHOR]