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

Yen, Andy
Choo, Ken-Loon
Yazdi, Shabnam K.
Franke, Patrick T.
Webster, Robert
Loh, Charles C. J.
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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.
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Research group Groupe Poblador Bahamonde
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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

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Deposited on : 2017-05-24

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