Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 21, Pages 9756-9765Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3018507
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Funding
- National Natural Science Foundation of China [20772036, 21172081]
- Produce and Learning and Research Project of Education Department of Guangdong Province [2011A090200039]
- Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education
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A novel iridium-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a variety of phenols was reported, which afforded the corresponding trans-2-phenoxy-1,2-dihydronaphthalen-1-ol products in high yields with moderate to excellent enantioselectivities (up to 98% ee) under mild conditions. The trans products are formed via the enantioselective cleavage of a bridgehead carbon-oxygen bond in 1 followed by S(N)2 nucleophilic attack by phenols. The effects of various bisphosphine ligands, Ag (I) salts, ammonium halides, bases, and solvents on the yield and enantioselectivity of the reaction were also investigated The trans configuration of the product 2a was confirmed by X-ray crystal structure analysis. A possible mechanism for the present catalytic reaction was proposed.
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