Borinic Acid-Catalyzed, Regioselective Ring Opening of 3,4-Epoxy Alcohols

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 nucleo...

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Bibliographic Details
Published in:Organic letters 2018-09, Vol.20 (17), p.5375-5379
Main Authors: Wang, Grace, Garrett, Graham E, Taylor, Mark S
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02295