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Synlett 1992; 1992(4): 306-308
DOI: 10.1055/s-1992-21349
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Regioselective Oxirane Ring Opening of trans-2,3-Epoxy Alcohols with Arylaluminum Complexes

Kyo Han Ahn* , Jeong Sook Kim, Chang Soo Jin, Dong Ho Kang, Do Soon Han, Yong Soon Shin, Dong Han Kim
  • *Department of Chemistry, Pohang Institute of Science and Technology, P.O. Box 125, Pohang 790-600, South Korea
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Publication Date:
08 March 2002 (online)

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Treatment of trans-2,3-epoxy alcohols 1, activated by triethylaluminum, with arylaluminum complexes 3 caused a regioselective ring-opening reaction at the 3-position to yield 3-aryl-1,2-alkanediols 4 in moderate yields. The activation of the epoxy ring by coordination with a Lewis acid appears to be essential for obtaining the desired product in a reasonable yield. White bulky substituents at the 3-position lowered the regioselectivity, a methoxy or methylenedioxy moiety on the arylaluminum complex 3 improved the regioselectivity drastically.