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Mechanism and Stereoselectivity of the BINOL-Catalyzed Allylboration of Skatoles
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-9349-7137
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 42017 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 21, p. 5904-5907Article in journal (Refereed) Published
Abstract [en]

Density functional theory calculations have been performed to investigate the binaphthol-catalyzed allylboration of skatoles. The high stereoselectivity observed for the reaction is reproduced well by the calculations and was found to be mainly a result of steric repulsions in the corresponding Zimmerman-Traxler transition states. The role of the additive MeOH in enhancing the stereoselectivity was also investigated and is suggested to promote the formation of less reactive allylboronic ester intermediates, thereby suppressing the formation of allylboroxine species, which undergo the facile racemic background reaction.

Place, publisher, year, edition, pages
2017. Vol. 19, no 21, p. 5904-5907
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-149991DOI: 10.1021/acs.orglett.7b02901ISI: 000414723900049PubMedID: 29039676OAI: oai:DiVA.org:su-149991DiVA, id: diva2:1168986
Available from: 2017-12-22 Created: 2017-12-22 Last updated: 2017-12-22Bibliographically approved

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Huang, GenpingDiner, ColinSzabó, Kálmán J.Himo, Fahmi
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