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Rhodium(II)‐Catalyzed Cycloaddition Reactions of Non‐classical 1,5‐Dipoles for the Formation of Eight‐Membered Heterocycles
Author(s) -
Lee Dong Jin,
Ko Donguk,
Yoo Eun Jeong
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.201506764
Subject(s) - cycloaddition , zwitterion , pyridinium , rhodium , intermolecular force , chemistry , catalysis , 1,3 dipolar cycloaddition , enol , computational chemistry , medicinal chemistry , organic chemistry , molecule
A new type of intermolecular rhodium(II)‐catalyzed [5+3] cycloaddition has been developed. This higher‐order cycloaddition between pyridinium zwitterion 1,5‐dipole equivalents and enol diazoacetates enables the formation of eight‐membered heterocyclic skeletons, which are otherwise difficult to construct. The optimized cycloaddition occurs efficiently under mild conditions with a wide range of pyridinium zwitterions and with high functional‐group tolerance.