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Stereocontrolled Synthesis of 1,3‐Diamino‐2‐ols by Aminohydroxylation of Bicyclic Methylene‐Aziridines
Author(s) -
Weatherly Cale D.,
Guzei Ilia A.,
Schomaker Jennifer M.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300416
Subject(s) - chemistry , aminal , stereoselectivity , bicyclic molecule , methylene , steric effects , norbornane , alkene , stereochemistry , diastereomer , pharmacophore , organic chemistry , catalysis
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 NaBH 4 to deliver the desired 1,3‐diamino‐2‐ols in good yields with high diastereomeric ratios.