An Efficient Synthesis of Optically Active Vicinal Diamine Arrays via Palladium-Catalyzed C-O to C-N Bond Transformation

Abstract

Optically active vicinal diamine arrays have been provided efficiently via palladium-catalyzed C-O to C-N bond transformation.

syn and anti 4-t-butoxycarbamoyl-3-hydroxy-1-alkenes - π-allylpalladium complex - trans imidazolidin-2-ones

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Relevant works based on a similar concept have been reported; that is, palladium-catalyzed reaction of a vinyl epoxide or a 4-pentene-1,3-diol carbonate in the presence of an isocyanate provides an initial zwitterion of π-allyl-palladium complex whose oxygen anion is then trapped with isocyanate to give a second π-allylpalladium complex bearing a nitrogen nucleophile tethered to the oxygen. Intramolecular attack of the nitrogen nucleophile to the π-allylpalladium complex furnishes a five- or six-membered carbamate:

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