Synthesis of azetidine, pyrrolidines and piperidine by intramolecular cyclization of ω-Azidoboranes.
This paper describes the development of efficient routes to azetidine, pyrrolidines and piperidines by creation of a carbon-nitrogen bond.Two complementary syntheses of these heterocycles were studied : the cyclization of ω-azidoboronic esters by treatment with boron trichloride, and the one pot hydroboration of an ω-azidoalkene and intramolecular reductive alkylation.The scope and limitations of these two promising approaches are reported.Keywords: azides / boronic esters / boranes / intermolecular cyclization / azetidine / pyrrolidine / piperidine / pyrrolizidine
Jego, J. M.,Carboni, B.,Vaultier, M.
p. 554 - 565
(2007/10/02)
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