Title: Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate.
Authors: Leverenz, Malte; Masson, Guillaume; Pardo, Domingo Gomez; Cossy, Janine
Abstract: 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.
Subjects: ALKOXIDES; DERIVATIZATION; CARBOXYLATES; NUCLEOPHILES; AMINES; PHOSPHONATES
Publication: Chemistry - A European Journal, 2021, Vol 27, Issue 66, p16325
ISSN: 0947-6539
Publication type: Academic Journal
DOI: 10.1002/chem.202102739

Synthesis of Azocanes from Piperidines via an Azetidinium Intermediate.

Leverenz, Malte; Masson, Guillaume; Pardo, Domingo Gomez; Cossy, Janine