Synthesis of 1,3-Diaminated Stereotriads <i>via</i> Rearrangement of 1,4-Diazaspiro[2.2]pentanes

Abstract

The synthesis of 1,3-diaminated stereotriads <i>via</i> the bis-aziridination of allenes is reported. The reactive 1,4-diazaspiro[2.2]pentane intermediates undergo a mild Brønsted acid-promoted rearrangement to yield 1,3-diaminated ketones in good yields with excellent stereocontrol. Directed reduction of the ketone can be achieved to yield a C–N/C–O/C–N stereotriad in high <i>dr</i>. The ability to transfer the axial chirality of the substrates to the products allows for the facile preparation of enantioenriched stereotriads from allenes in two simple steps