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Rhodium‐Catalyzed Enantioselective Isomerization of meso ‐Oxabenzonorbornadienes to 1,2‐Naphthalene Oxides
Author(s) -
Yen Andy,
Choo KenLoon,
Yazdi Shabnam K.,
Franke Patrick T.,
Webster Robert,
Franzoni Ivan,
Loh Charles C. J.,
PobladorBahamonde Amalia I.,
Lautens Mark
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700632
Subject(s) - isomerization , rhodium , enantioselective synthesis , naphthalene , catalysis , chemistry , medicinal chemistry , organic chemistry
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.