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