Access to Enantio-enriched Substituted α-Trifluoromethyl Azepanes from l-Proline
Guillaume Masson1, Sarah Rioton1, Domingo Gomez Pardo1
1Laboratoire de Chimie Organique, Institute of Chemistry , Biology and Innovation (CBI), UMR 8231, ESPCI Paris/CNRS, PSL University , 10 rue Vauquelin , Paris 75231 Cedex 05, France.
Abstract:
4-Substituted α-trifluoromethyl azepanes C were synthesized via the ring expansion of trifluoromethyl pyrrolidines A, which were synthesized from l-proline via a regioselective ring-opening of a bicyclic azetidinium intermediate B by various nucleophiles. The regioselectivity of the ring expansion is induced by the presence of a trifluoromethyl group. The chirality of the starting material was transferred to the azepanes with high enantiomeric excess.
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