Syntheses and reactions of new optically active terpene dialkyl diselenides

Abstract

The reaction of sodium diselenide with optically active alkyl tosylates or chlorides is found to be a useful method for the synthesis of optically active dialkyl diselenides. Optically active monoterpene diselenides derived from menthane, carane, pinane, and bornane systems have been obtained. The influence of the terpene fragment of the obtained diselenides on the diastereomeric excess of the methoxyselenylation products has been investigated. The best result for methoxyselenylation was observed for (-)-diisopinocamphyl diselenide. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.