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Regioselective Oxirane Ring Opening of trans-2,3-Epoxy Alcohols with Arylaluminum Complexes
08 March 2002 (online)
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.