Organic Letters
Organic Letters
4 years ago

Mechanism and Stereoselectivity of the BINOL-Catalyzed Allylboration of Skatoles

Mechanism and Stereoselectivity of the BINOL-Catalyzed Allylboration of Skatoles
Genping Huang, Kálmán J. Szabó, Fahmi Himo, Colin Diner
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02901

DOI: 10.1021/acs.orglett.7b02901

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