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- Title
Stereocontrolled Synthesis of 1,3-Diamino-2-ols by Aminohydroxylation of Bicyclic Methylene-Aziridines.
- Authors
Weatherly, Cale D.; Guzei, Ilia A.; Schomaker, Jennifer M.
- Abstract
Nitrogen-containing stereotriads, which are defined as compounds with three adjacent stereodefined carbon atoms, are common structural motifs in several biologically relevant compounds. The 1,3-diamino-2-ol motif in particular is an important pharmacophore for which there are limited stereoselective synthetic approaches. In this communication, we describe the aminohydroxylation of a series of bicyclic methylene-aziridines obtained from the aziridination of a series of homoallenic carbamates. The unusual electronic and steric features of these useful heterocyclic scaffolds render the Os-catalyzed aminohydroxylation of the exocyclic alkene highly regio- and stereoselective. Rearrangement of the proposed N,O-aminal intermediate to a 1,3-diamino-2-one is followed by reduction with NaBH4 to deliver the desired 1,3-diamino-2-ols in good yields with high diastereomeric ratios.
- Subjects
DIAMINO amino acids; HETEROCHAIN polymers; REGIOSELECTIVITY (Chemistry); OXIDATION; AZIRIDINATION; STEREOSELECTIVE reactions
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 18, p3667
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300416