Rhodium-Catalyzed Enantioselective Isomerization of meso-Oxabenzonorbornadienes to 1,2-Naphthalene Oxides.
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.
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Andy
0000-0002-6404-9191
A
Yen
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Ken-Loon
KL
Choo
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Shabnam K
SK
Yazdi
Carbogen Amcis AG, Hauptstraße 171, 4416, Bubendorf, Switzerland.
Patrick T
PT
Franke
Bayer Pharma Aktiengesellschaft, Aprather Web 18a, 42113, Wuppertal, Germany.
Robert
R
Webster
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Ivan
0000-0001-8110-6218
I
Franzoni
Technische Universität Dortmund, Otto-Hahn-Straße 4a, 44227, Dortmund, Germany.
Charles C J
0000-0001-6970-1989
CCJ
Loh
Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211, Geneva, Switzerland.
Amalia I
AI
Poblador-Bahamonde
Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Mark
0000-0002-0179-2914
M
Lautens
allylic compounds; asymmetric catalysis; enantioselectivity; isomerization; rhodium