Low Catalyst Loadings in Olefin Metathesis: Synthesis of Nitrogen Heterocycles by Ring-Closing Metathesis was written by Kuhn, Kevin M.;Champagne, Timothy M.;Hong, Soon Hyeok;Wei, Wen-Hao;Nickel, Andrew;Lee, Choon Woo;Virgil, Scott C.;Grubbs, Robert H.;Pederson, Richard L.. And the article was included in Organic Letters in 2010.Synthetic Route of C10H17NO2 This article mentions the following:
Ruthenium carbene complexes are compared for their effectiveness as catalysts for the ring-closing metathesis reactions of Boc-protected amines to give Boc-pyrrolidines, Boc-tetrahydropyridines, and Boc-tetrahydroazepines with disubstituted, trisubstituted, and tetrasubstituted olefin moieties. In some cases, ring-closing metathesis reactions are performed with catalyst loadings as low as 0.05 mol.% to give >90% yields of nitrogen heterocycles; tetrasubstituted alkene products require 0.1-0.5 mol.% catalyst loadings to obtain good yields of product. Ring-closing metathesis reactions of bisallylic carbamates to give Boc-pyrrolines could be performed neat, while the corresponding reactions of allylic homoallylic carbamates to give Boc-tetrahydropyridines could be performed at substrate concentrations of 1.0 M and the corresponding reactions of bishomoallylic carbamates to give Boc-tetrahydroazepines work best at substrate concentrations of 0.05-0.2 M. Me tert-Bu ether is used as a solvent in some of the ring-closing metathesis reactions instead of toluene. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Synthetic Route of C10H17NO2).
tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ闁荤姾娅ｅΛ纭俵闂? in pyridine vs. 150 kJ闁荤姾娅ｅΛ纭俵闂? in benzene). One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Synthetic Route of C10H17NO2