Ring Opening of Aziridines by Pendant Sulfamates Allows for Regioselective and Stereospecific Preparation of Vicinal Diamines
Someshwar Nagamalla, Annu Anna Thomas, Appasaheb K. Nirpal, Joel T. Mague, Shyam Sathyamoorthi
Abstract
The ring opening of aziridines by pendant sulfamates is a viable strategy for the rapid preparation of vicinal diamines. Our reaction is compatible with both disubstituted cis - and trans -aziridines; unsubstituted, N -alkyl, and N -aryl sulfamates engage effectively. In all cases examined, the cyclization reaction is perfectly regioselective and stereospecific. Once activated, the product oxathiazinane heterocycles can be ring opened with a diverse range of nucleophiles.
Topics & Concepts
RegioselectivityChemistryStereospecificityVicinalNucleophileRing (chemistry)AlkylArylStereochemistryMedicinal chemistryOrganic chemistryCatalysisSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques