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- 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