Amine-Catalyzed Phospha-Michael Reaction of α,β-Unsaturated Aldehydes and Ketones with Multifunctional N-Heterocyclic Phosphine-Thioureas as Phosphonylation Reagent

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An efficient amine-catalyzed phospha-Michael addition reaction of α,β-unsaturated aldehydes/ketones with N-heterocyclic phosphines for the synthesis of Î-ketodiazaphosphonates has been developed. With freedom from nucleophile additives, this mild process affords a range of structurally diverse Î-ketodiazaphosphonates in moderate to excellent yields. Importantly, various α,β-unsaturated ketones were also tolerated in this process and gave moderate yields. © 2016 American Chemical Society.