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Syntheses and Reactions of New Optically Active Terpene Dialkyl Diselenides
Author(s) -
Ścianowski Jacek,
Rafiński Zbigniew,
Wojtczak Andrzej
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600044
Subject(s) - chemistry , optically active , diselenide , terpene , diastereomer , alkyl , organic chemistry , monoterpene , selenium , stereochemistry
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, 69451 Weinheim, Germany, 2006)