Experimental study demonstrates asymmetric ring-opening of azabicyclic alkenes with phenols, indicating a direct catalytic route to chiral phenoxyamino compounds.
The asymmetric ring-opening of azabicyclic alkenes with a variety of phenols is investigated using an iridium catalyst generated in situ from 2.5 mol % of [Ir(COD)Cl] 2 and 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 4b was confirmed by X-ray crystallography.
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Fang et al. (2012) studied this question.
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