Rhodium-Catalyzed Enantioselective Isomerization of <i>meso</i>-Oxabenzonorbornadienes to 1,2-Naphthalene Oxides

Yen, Andy; Choo, Ken-Loon; Yazdi, Shabnam K.; Franke, Patrick T.; Webster, Robert; Franzoni, Ivan; Loh, Charles C. J.; Poblador Bahamonde, Amalia Isabel; Lautens, Mark

doi:10.1002/anie.201700632

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Title		Rhodium-Catalyzed Enantioselective Isomerization of meso-Oxabenzonorbornadienes to 1,2-Naphthalene Oxides
Authors		Yen, Andy Choo, Ken-Loon Yazdi, Shabnam K. Franke, Patrick T. Webster, Robert Franzoni, Ivan Loh, Charles C. J. Poblador Bahamonde, Amalia Isabel Lautens, Mark show all authors [1 - 9]
Published in		Angewandte Chemie: International Edition. 2017, vol. 56, no. 22, p. 6307-6311
Abstract		Herein we describe a rhodium-catalyzed enantioselective isomerization of meso-oxabicyclic alkenes to 1,2-naphthalene oxides. These potentially useful building blocks can be accessed in moderate to excellent yields with impressive enantioselectivities. Additionally, experimental findings supported by preliminary computations suggest that ring-opening reactions of bridgehead disubstituted oxabicyclic alkenes proceed through the intermediacy of these epoxides and may point to a kinetically and thermodynamically favored reductive elimination as the origin for the observed enantioselectivities.
Identifiers		DOI: 10.1002/anie.201700632
Full text		Article (Published version) (1.1 MB) - Limited access to UNIGE
Structures		Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
Research group		Groupe Poblador Bahamonde
Citation (ISO format)		YEN, Andy et al. Rhodium-Catalyzed Enantioselective Isomerization of meso-Oxabenzonorbornadienes to 1,2-Naphthalene Oxides. In: Angewandte Chemie: International Edition, 2017, vol. 56, n° 22, p. 6307-6311. doi: 10.1002/anie.201700632 https://archive-ouverte.unige.ch/unige:94490