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

Ryan J FradetteMinkyu KangFrederick G West

Published in: Angewandte Chemie (International ed. in English) (2017)

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.

Keyphrases

hydrogen peroxide
electron transfer
visible light
nitric oxide
anti inflammatory