Stereoselective two-carbon ring expansion of allylic amines via electronic control of palladium-promoted equilibria?
Chemical Science Pub Date: 2023-06-06 DOI: 10.1039/D3SC02303F
Abstract
General methodologies enabling the two-carbon homologation of pyrrolidine and piperidine systems have yet to be developed. Herein we report that palladium-catalysed allylic amine rearrangements enable efficient two-carbon ring expansion of 2-alkenyl pyrrolidine and piperidines to their azepane and azocane counterparts. Conditions are mild, tolerant of a range of functional groups and the process can occur with high enantioretention. The products formed undergo a range of orthogonal transformations, making them ideal scaffolds for the creation of compound libraries.
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Journal Name：Chemical Science
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CAS no.: 89640-58-4
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