113965-36-9Relevant articles and documents
Asymmetric synthesis of 2-substituted piperidines using a multi-component coupling reaction: Rapid assembly of (S)-coniine from (S)-1-(1-phenylethyl)-2-methyleneaziridine
Hayes,Shipman,Twin
, p. 1784 - 1785 (2001)
(S)-Coniine is made using a reaction which assembles the piperidine ring by the sequential formation of four new chemical bonds and installs the C-2 stereogenic centre with high levels of diastereocontrol (90% de).
An Asymmetric Synthesis of 2-Substituted Piperidines through Ozonolysis of Cyclopentenes and Reductive Aminocyclization
Kawaguchi, Mamoru,Hayashi, Osamu,Sakai, Noriyuki,Hamada, Masayuki,Yamamoto, Yukio,Oda, Jun'ichi
, p. 3107 - 3112 (2007/10/02)
By the action of ozone, sodium cyanoborohydride and the optically active benzylic amines 2, the 1-substituted cyclopentenes 1, 5 and 9 were converted to a diastereometric mixture of 1,2-disubstituted piperidines (3, 6 and 10), respectively.Hydrogenation of these compounds and the following work-up yielded optically active 2-alkylpiperidines (4, up to 68percente.e.), pipecolic acid (7, 84percent e.e.) and 2-(hydroxymethyl)piperidine (11, up to 85percente.e.).Chromatographic separation of the major isomers of 3b and 6 enabled optically pure coniine (4b) and pipecolic acid (7) to be prepared, respectively.