5 years ago

Oxidation-Initiated Cyclizations of Pentadienyl Ethers: An Alternative Entry to the Nazarov Reaction

Oxidation-Initiated Cyclizations of Pentadienyl Ethers: An Alternative Entry to the Nazarov Reaction
Ryan J. Fradette, Minkyu Kang, F. G. West
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 MnO2 as terminal oxidant is also described. Dehydrogenative Nazarov reaction: 1,4-Pentadien-3-yl ethers undergo oxidative conversion to the corresponding 3-alkoxypentadienyl cations followed by clean Nazarov cyclization and regioselective exocyclic elimination to furnish alkylidene cyclopentenol ethers with the net loss of H2. This method provides mild, Lewis acid-free access to Nazarov products in which the stereogenic centers formed in the electrocyclization are preserved.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701748

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