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Synthesis 2009(21): 3684-3688  
DOI: 10.1055/s-0029-1217011
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regio- and Stereoselectivity in Phenylselenoetherification of (Z)- and (E)-Hex-4-en-1-ols

Vera M. Divac, Zorica M. Bugarčić*
University of Kragujevac, Faculty of Science, Department of Chemistry, Radoja Domanovića 12, P.O. Box 60, 34 000 Kragujevac, Serbia
Fax: +381(34)335040; e-Mail: zoricab@kg.ac.rs;
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Publication History

Received 17 June 2009
Publication Date:
23 September 2009 (online)

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Abstract

Δ4-Primary alkenols (Z)- and (E)-hex-4-en-1-ols underwent facile cyclization to the corresponding phenyl selenoethers using PhSeX (X = Cl, Br) in high yields and in good to excellent selectivities in the presence of some catalysts (Lewis acids and bases). The reaction succeeded in complete control of stereo- and regioselectivity. The best results were obtained with triethylamine and tin(II) chloride. Triethylamine as an additive in the reaction with (Z)-hex-4-en-1-ol gives only erythro-2-[1-(phenylseleno)ethyl]tetrahydrofuran, while the E-isomer gives cis-2-methyl-3-(phenylseleno)tetrahydropyran in large excess. Tin(II) chloride as an additive in the reaction with (Z)-hex-4-en-1-ol gives threo-2-[1-(phenylseleno)ethyl]tetrahydrofuran and with the E-isomer gives trans-2-methyl-3-(phenylseleno)tetrahydropyran. The reactions were performed under very mild experimental conditions, and the obtained yields were almost quantitative.

Key words

alcohol - cyclization - heterocycles - regioselectivity - Lewis acids

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