Synthesis of enantiomerically pure β-azidoselenides starting from natural terpenes

M Tiecco, L Testaferri, C Santi, C Tomassini, S Santoro…

Index: Tiecco, Marcello; Testaferri, Lorenzo; Santi, Claudio; Tomassini, Cristina; Santoro, Stefano; Marini, Francesca; Bagnoli, Luana; Temperini, Andrea Tetrahedron, 2007 , vol. 63, # 50 p. 12373 - 12378

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Citation Number: 11

Abstract

Several unsaturated natural terpenes have been easily converted, in good yields, into the corresponding enantiomerically pure β-azidoselenides by addition of the electrophilic selenium reagent PhSeOTf in the presence of sodium azide. These reactions are stereospecific anti additions, which occur with a Markovnikov orientation. Examples of the synthetic importance of these β-azidoselenides are also reported.