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Rhodium(III)‐Catalyzed Alkenyl CH Bond Functionalization: Convergent Synthesis of Furans and Pyrroles
Author(s) -
Lian Yajing,
Huber Tatjana,
Hesp Kevin D.,
Bergman Robert G.,
Ellman Jonathan A.
Publication year - 2013
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.201207995
Subject(s) - annulation , chemistry , catalysis , tetrahydrofuran , aromatization , tosyl , medicinal chemistry , rhodium , amine gas treating , alcohol , organic chemistry , surface modification , pyrrole , solvent
Ring in the new : A new annulation for the efficient synthesis of substituted furans and pyrroles is reported. The Rh III ‐catalyzed reaction of O‐methyl α,β‐unsaturated oximes with aldehydes and N‐tosyl imines affords secondary alcohol and amine intermediates, respectively. Cyclization and aromatization occurs under the reaction conditions to provide access to biologically relevant furans and pyrroles in good yields. Cp*=C 5 Me 5 , DCE=1,2‐dichloroethane, THF=tetrahydrofuran.