Rhodium‐Catalyzed Enantioselective Isomerization of meso‐Oxabenzonorbornadienes to 1, 2‐Naphthalene Oxides. (20th March 2017)

• Record Type: Journal Article
• Authors: Yen, Andy; Choo, Ken‐Loon; Yazdi, Shabnam K.; Franke, Patrick T.; Webster, Robert; Franzoni, Ivan; Loh, Charles C. J.; Poblador‐Bahamonde, Amalia I.; Lautens, Mark
• Is Part Of: Angewandte Chemie. Volume 129:Number 22(2017)
• Page Start: 6404
• Page End: 6408
• Publication Date: 2017-03-20
• Subjects: Allylverbindungen -- Asymmetrische Katalyse -- Enantioselektivität -- Isomerisierungen -- Rhodium; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201700632
• Languages: English
• ISSNs: 0044-8249

Abstract

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.