Ontology highlight
ABSTRACT:
SUBMITTER: Weatherly CD
PROVIDER: S-EPMC4490830 | biostudies-literature | 2012 Apr
REPOSITORIES: biostudies-literature
Weatherly Cale D CD Rigoli Jared W JW Schomaker Jennifer M JM
Organic letters 20120320 7
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 enantioenri ...[more]