4.5 Article

Iridium-Catalyzed Asymmetric Ring-Opening of Azabicyclic Alkenes with Phenols

Journal

ORGANOMETALLICS
Volume 31, Issue 8, Pages 3113-3118

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/om3000295

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Funding

  1. National Natural Science Foundation of China [21172081, 20802021]
  2. Education Department of Guangdong Province [2011A090200039]

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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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