Solvent- and structure-dependent regioselectivity in the boron-mediated aldol reaction of 2-(1,3-dioxolan-2-yl)ethyl ethyl ketones

S. Lanners, H. Norouzi-Arasi, N. Khiri, G. Hanquet

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    Abstract

    The regioselectivity of the ChxBCl/EtN-mediated (Chx = cyclohexyl) aldol reactions of ketones of general structure 2 has been studied and was shown to depend on both ketone structure and solvent. Useful levels of regioselectivity in favour of any of the two possible regioisomers were obtained in either pentane or diethyl ether. The relative configuration of the aldol products was assigned by H NMR studies of six-membered-ring derivatives. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
    Original languageEnglish
    Pages (from-to)4065-4075
    Number of pages11
    JournalEuropean Journal of Organic Chemistry
    Volume2007
    Issue number24
    DOIs
    Publication statusPublished - 1 Jan 2007

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