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Phenol-Containing Macrocyclic Diamides as New Catalysts in the Highly Regioselective Conversion of Epoxides to β-Hydroxy Thiocyanates

Hashem Sharghi*, Mohammad Ali Nasseri and Khodabakhsh Niknam

*Department of Chemistry, Shiraz University, Shiraz 71454, I.R. Iran, and Department of Chemistry, Persian Gulf University, Bushehr 75168, I.R. Iran

H. Sharghi, M. A. Nasseri, K. Niknam, J. Org. Chem., 2001, 66, 7287-7293.

DOI: 10.1021/jo0103266

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Individual β-hydroxy thiocyanates can be synthesized in high yield and with more than 90% regioselectivity in the presence of phenol-containing macrocyclic diamides under mild reaction conditions. The method offers high regioselectivity, simple regeneration/reuse of catalyst through several cycles without a decrease in activity, and ease of workup of the reaction.

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Key Words

thiocyanates, organocatalysis

ID: J42-Y2001