title: Exploiting Distal Reactivity of Coumarins: A Rhodium-Catalyzed Vinylogous Asymmetric Ring-Opening Reaction.
abstract: While the utility of vinylogous enolates is well established in the setting of vinylogous aldol, Mannich, and Michael chemistries, literature reports concerning γ-reactivity are scarce for other reaction classes. Presented herein is an unprecedented example of vinylogous reactivity exemplified by the rhodium-catalyzed asymmetric ring-opening reaction of oxabicycles. This strategy also provides a powerful route to incorporate the biologically useful coumarin motif into the hydronapthalene scaffold.
authors.affiliation: Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Charles C J
authors.initials: CC
authors.lastname: Loh
authors.affiliation: Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Matthias
authors.initials: M
authors.lastname: Schmid
authors.affiliation: Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Brendan
authors.initials: B
authors.lastname: Peters
authors.affiliation: Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.|Laboratory for Advanced Material and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China.
authors.forename: Xiang
authors.initials: X
authors.lastname: Fang
authors.affiliation: Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada. mlautens@chem.utoronto.ca.
authors.forename: Mark
authors.identifier: http://orcid.org/0000-0001-9867-9178
authors.initials: M
authors.lastname: Lautens
keywords: enantioselectivity; heterocycles; rhodium; ring-opening reactions; synthetic methods