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Asymmetric Syntheses with a New Nitrogen Containing Chiral Diselenide
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1  Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, I- 06123-Perugia, Italy

Abstract: Organoselenium reagents are largely used in organic synthesis to introduce new functional groups into organic substrates under very mild experimental conditions.[1] In recent years, several research groups have described the synthesis of a number of chiral non racemic diselenides which can be transformed in situ into electrophilic selenenylating agents to effect efficient asymmetric syntheses.[2][3][4][5][6][7] Diselenides containing a nitrogen atom in the chiral moiety have also been employed as useful ligands in various transformations such as diethilzinc additions to aldehydes,[8] asymmetric hydrosilylation[9] and transfer hydrogenation reactions.[10] Moreover these diselenides can also be employed in the sequential catalytic stereoselective oxyselenenylation-elimination reactions using ammonium persulfate to generate the electrophilic selenenylating species and to promote the elimination process.[11] Herein we report the synthesis of two new chiral nitrogen containing diselenides and the use of these compounds as precursors of electrophilic species in asymmetric additions of organoselenium reagents to olefins.
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