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Paper | Special issue | Vol 52, No. 2, 2000, pp.621-632
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S55
Selective Intramolecular Oxyselenenylation of Olefinic Alcohols and Carboxylic Acids by Using Organic Cyanoselenides in the Presence of Metal Triflates

Shizuaki Murata,* Chisato Suzuki, Hirofumi Inoue, Yukihiro Andoh, Yoshihiro Hayasi, and Toshiyasu Suzuki

*Graduate School of Human Informatics, Nagoya University, Nagoya 464-8601, Japan

Abstract

The reagent, ArSeCN—M(OTf)n, is prepared from equimolar amounts of an aromatic selenocyanate and metal trifluoromethanesulfonate. It reacts with unsaturated alcohols and carboxylic acids to give cyclic ethers and lactones, respectively. Depending on conditions, reactions of trans-2-allylcyclohexanol with the reagent selectively afford exo-cyclized tetrahydrofuran or endo-cyclized tetrahydropyran. The mechanism of exo/endo selection is discussed based on molecular dynamics studies.