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Oxidation‐Initiated Cyclizations of Pentadienyl Ethers: An Alternative Entry to the Nazarov Reaction
Author(s) -
Fradette Ryan J.,
Kang Minkyu,
West F. G.
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.201701748
Subject(s) - cyclopentanone , chemistry , regioselectivity , stereocenter , catalysis , methylene , organic chemistry , annulation , medicinal chemistry , enantioselective synthesis
Oxidation‐initiated Nazarov reactions of 1,4‐pentadien‐3‐yl ethers take place in the presence of DDQ. Termination by regioselective elimination preserves both stereocenters created during electrocyclization, providing cyclopentanone products bearing an exocyclic methylene unit. Use of catalytic DDQ with MnO 2 as terminal oxidant is also described.