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Borinic Acid-Catalyzed, Regioselective Ring Opening of 3,4-Epoxy Alcohols
Grace Wang1, Graham E Garrett1, Mark S Taylor1
1Department of Chemistry , University of Toronto , 80 St. George St ., Toronto , Ontario M5S 3H6 , Canada.
Abstract:
Diarylborinic acids (Ar2BOH) catalyze the C3-selective ring opening of 3,4-epoxy alcohols with aniline, dialkylamine and arenethiol nucleophiles. The regiochemical outcome is consistent with a catalytic tethering mechanism in which the borinic acid interacts with both the electrophile and the nucleophile. The rate acceleration resulting from this induced intramolecularity effect is sufficient to overcome steric biases that would otherwise favor C4-selective opening of the substituted epoxy alcohols.
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