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

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

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 mod...

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Veröffentlicht in:Organometallics 2012-04, Vol.31 (8), p.3113-3118
Hauptverfasser: Fang, Shai, Liang, Xiuli, Long, Yuhua, Li, Xiaolu, Yang, Dingqiao, Wang, Sanyong, Li, Chunrong
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container_end_page 3118
container_issue 8
container_start_page 3113
container_title Organometallics
container_volume 31
creator Fang, Shai
Liang, Xiuli
Long, Yuhua
Li, Xiaolu
Yang, Dingqiao
Wang, Sanyong
Li, Chunrong
description 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.
doi_str_mv 10.1021/om3000295
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title Iridium-Catalyzed Asymmetric Ring-Opening of Azabicyclic Alkenes with Phenols
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