1000291-89-3Relevant articles and documents
Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate
Leverenz, Malte,Masson, Guillaume,Pardo, Domingo Gomez,Cossy, Janine
, p. 16325 - 16328 (2021/10/25)
α-Trifluoromethyl azocanes are accessible from 2-(trifluoropropan-2-ol) piperidines by metal-free ring-expansion involving a bicyclic azetidinium intermediate. The opening of the azetidinium intermediate was achieved by various nucleophiles (amines, alcoholates, carboxylates, phosphonates, halides and pseudo-halides) with an excellent regio- diastereo- and enantioselectivity and in good yields. The relative configuration of the piperidines and azocanes were assigned and the deprotected azocanes offer opportunities for further derivatization.