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Asymmetric Ion Pair Catalysis of 6π Electrocyclizations: Brønsted Acid Catalyzed Enantioselective Synthesis of Optically Active 1,4-Dihydropyridazines

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  • Financial support from the DFG is acknowledged. A.D. and C.M.R.V. thank the Alexander von Humboldt Foundation for a fellowship. The absolute configuration was determined by I.A., and W.B. carried out the MS-measurements.

Abstract

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Electric slide: Described is a general, operationally simple, highly enantioselective Brønsted acid catalyzed condensation/6π-electrocyclization reaction between hydrazones and α,β-unsaturated aldehydes that yields valuable 1,4-dihydropyridazines. The reaction exhibits high tolerance towards functional groups and affords products with up to 98 % ee.

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