1228556-60-2Relevant articles and documents
Synthetic modifications of bifunctional homoallylamines: Synthesis of 2-arylpiperidines, (R)-anatabine and (R)-anabasine
Nallasivam, Jothi L.,Fernandes, Rodney A.
, p. 2815 - 2822 (2019)
The chiral homoallylamines with orthogonal bifunctional handle, an amine, and a pendant allyl unit are available to be easily converted into N-heterocycles. The N-allylation and Ru-catalyzed ring-closing metathesis delivered the bioactive 2-arylpiperidines, Nicotiana tabacum alkaloids (R)-anatabine and (R)-anabasine in three steps. A formal synthesis of (R)-N-methylanatabine and (R)-N-methylanabasine is also completed.
Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles
Heath, Rachel S.,Pontini, Marta,Hussain, Shahed,Turner, Nicholas J.
, p. 117 - 120 (2016/01/26)
A novel amine oxidase (AO)/imine reductase (IRED) system was developed for the deracemization of racemic amines. By combining (R)-6-hydroxy-d-nicotine oxidase (6-HDNO) with an (R)-IRED, a panel of racemic 2-substituted piperidines and pyrrolidines were deracemized to yield the (S)-amines in high yields and enantiomeric excess values. Other N-heterocycles were deracemized with monoamine oxidase (MAO-N) or 6-HDNO in combination with ammonia borane, which allowed comparison of the two enzyme deracemization approaches with that involving a chemical reducing agent.
Enantioselective allylation of imines catalyzed by newly developed (-)-β-pinene-based π-allylpalladium catalyst: An efficient synthesis of (R)-α-propylpiperonylamine and (R)-pipecolic acid
Fernandes, Rodney A.,Nallasivam, Jothi L.
, p. 7789 - 7800 (2013/04/23)
A newly developed π-allylpalladium with a (-)-β-pinene framework and an isobutyl side chain catalyzed the enantioselective allylation of imines in good yields and enantioselectivities (20 examples, up to 98% ee). An efficient enantioselective synthesis of the (R)-α-propyl piperonylamine part of DMP 777, a human leukocyte elastase inhibitor and (R)-pipecolic acid have been achieved as a useful application of this methodology. The Royal Society of Chemistry 2012.
