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Rhodium(II)‐Catalyzed Enantioselective Synthesis of Troponoids
Author(s) -
Murarka Sandip,
Jia ZhiJun,
Merten Christian,
Daniliuc ConstantinG.,
Antonchick Andrey P.,
Waldmann Herbert
Publication year - 2015
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.201502233
Subject(s) - tropone , enantioselective synthesis , cycloaddition , rhodium , moiety , chemistry , stereoselectivity , catalysis , yield (engineering) , stereochemistry , organic chemistry , materials science , metallurgy
We report a rhodium(II)‐catalyzed highly enantioselective 1,3‐dipolar cycloaddition reaction between the carbonyl moiety of tropone and carbonyl ylides to afford troponoids in good to high yields with excellent enantioselectivity. We demonstrate that α‐diazoketone‐derived carbonyl ylides, in contrast to carbonyl ylides derived from diazodiketoesters, undergo [6+3] cycloaddition reactions with tropone to yield the corresponding bridged heterocycles with excellent stereoselectivity.