1000291-89-3Relevant academic research and scientific papers
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.
Gram-Scale Synthesis of the (?)-Sparteine Surrogate and (?)-Sparteine
Firth, James D.,Canipa, Steven J.,Ferris, Leigh,O'Brien, Peter
supporting information, p. 223 - 226 (2017/12/29)
An 8-step, gram-scale synthesis of the (?)-sparteine surrogate (22 % yield, with just 3 chromatographic purifications) and a 10-step, gram-scale synthesis of (?)-sparteine (31 % yield) are reported. Both syntheses proceed with complete diastereocontrol and allow access to either antipode. Since the syntheses do not rely on natural product extraction, our work addresses long-term supply issues relating to these widely used chiral ligands.
