title: Synthesis of 1,3-diaminated stereotriads via rearrangement of 1,4-diazaspiro[2.2]pentanes.
abstract: The synthesis of 1,3-diaminated stereotriads via 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 dr. 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.
authors.affiliation: Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.
authors.forename: Cale D
authors.initials: CD
authors.lastname: Weatherly
authors.forename: Jared W
authors.initials: JW
authors.lastname: Rigoli
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Schomaker
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D048289:Imidazolidines / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*
chemical_list: C572470:(2R,3S,4'S)-hydroxyenduracididine; D000466:Alkadienes; D001372:Aza Compounds; D048289:Imidazolidines; D007659:Ketones; D011743:Pyrimidines; D011758:Pyrroles; D013141:Spiro Compounds; C520151:manzacidin B; C025947:propadiene