Ritter Reaction on Terpenoids. III. Stereospecific Preparation of Bicyclic[3.3.1]Substituted Piperidines.

SAMANIEGO, WALTER NUMAS; BALDESSARI, ALICIA; PONCE, MARÍA ALEJANDRA; RODRIGUEZ, JUAN BAUTISTA; GROS, EDUARDO GERVASIO; CARAM, JOSÉ A.; MARSCHOFF, CARLOS M.

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 1994 vol. 35 p. 6967 - 6970

0040-4039

Treatment of chiral monoterpenes with different nitrile compounds in the  presence of perchlonc acid atfords (lS,5R,8R) 8-alkyl(aryl)-2alkyl(aryl)-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3. l]non-2-ene or the corresponding (lR 5S,8S) enantiomer. The respective free imines yield optically pure piperidines derivatives when treated with reducing agaents (NaBH4, NaCNBH3).presence of perchlonc acid atfords (lS,5R,8R) 8-alkyl(aryl)-2alkyl(aryl)-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3. l]non-2-ene or the corresponding (lR 5S,8S) enantiomer. The respective free imines yield optically pure piperidines derivatives when treated with reducing agaents (NaBH4, NaCNBH3).