Organoselenium mediated asymmetric cyclizations. Synthesis of enantiomerically pure 1, 6-dioxaspiro [4.4] nonanes

…, L Testaferri, L Bagnoli, C Scarponi, A Temperini…

Index: Tiecco, Marcello; Testaferri, Lorenzo; Bagnoli, Luana; Scarponi, Catalina; Temperini, Andrea; Marini, Francesca; Santi, Claudio Tetrahedron Asymmetry, 2006 , vol. 17, # 19 p. 2768 - 2774

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Citation Number: 14

Abstract

The asymmetric cyclization of 1-hydroxyoct-7-en-4-one, promoted by camphorselenenyl tetrafluoroborate, generated from camphor diselenide and silver tetrafluoroborate in dichloromethane at room temperature, afforded a mixture of two diastereoisomeric E-and two diastereoisomeric Z-2-[(camphorseleno) methyl]-1, 6-dioxaspiro [4.4] nonanes. These were separated by medium pressure liquid chromatography and then deselenenylated ...