1214914-47-2Relevant articles and documents
Preparation of enantiopure substituted piperidines containing 2-alkene or 2-alkyne Chains: Application to total syntheses of natural quinolizidine- alkaloids
Cheng, Guolin,Wang, Xinyan,Su, Deyong,Liu, Hui,Liu, Fei,Hu, Yuefei
, p. 1911 - 1916 (2010)
"Chemical Equation Presented" A general method, for the preparation of enantiopure 2-alkene- or 2-alkyne-containing chain substituted piperidines was established by using nonracemic Betti base as a chiral auxiliary. The key step is that the auxiliary residue was removed by a novel base-catalyzed N-debenzylation via a formation of o-quinone methide mechanism in stead, of the traditional hydrogenolysis, by which the alkene or alkyne groups survived. By this method, ten 2-alkene- or 2-alkyne-containing chain substituted piperidines were prepared on the gram scale within a few hours. To demonstrate the efficiency of the method and the versatility of the product, total, syntheses of natural alkaloids (+)-pelletierine((-)-lasubine II, and (-)-cermizine C were achieved by using (S)-2-allyl-N-Bocpiperidine as a versatile building block.