3 years ago

Rhodium-Catalyzed Enantioselective Isomerization of meso-Oxabenzonorbornadienes to 1,2-Naphthalene Oxides

Rhodium-Catalyzed Enantioselective Isomerization of meso-Oxabenzonorbornadienes to 1,2-Naphthalene Oxides
Shabnam K. Yazdi, Ivan Franzoni, Patrick T. Franke, Andy Yen, Amalia I. Poblador-Bahamonde, Mark Lautens, Ken-Loon Choo, Robert Webster, Charles C. J. Loh
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. An enantioselective isomerization of bridgehead-disubstituted meso-oxabicyclic alkenes catalyzed by a cationic [Rh(cod)2]OTf/(R)-(S)-PPF-PtBu2 catalyst system is described. The enantioenriched 1,2-naphthalene oxide products are potentially useful building blocks in asymmetric synthesis. The involvement of these epoxides as intermediates in asymmetric ring opening reactions of oxabicyclic alkenes is also explored.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700632

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