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Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer
journal contribution
posted on 2017-02-21, 20:14 authored by Seung
Wook Kim, Wonchul Lee, Michael J. KrischeGlycidols
prepared via Sharpless asymmetric epoxidation participate
in asymmetric redox-neutral carbonyl allylation with good levels of
catalyst-directed diastereoselectivity. Equally stereoselective allylations
may be performed from the aldehyde oxidation level using 2-propanol
as the terminal reductant. An epoxide ring-opening reaction using
AlMe3-n-BuLi is used to prepare the propionate-based
stereotetrad spanning C17–C23 of dictyostatin, illustrating
how this method may be applied to polyketide construction.
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Allyl Acetateterminal reductantBuLiepoxide ring-opening reactiondictyostatinIridium-Catalyzed Hydrogen Transfer Glycidolsredox-neutral carbonyl allylationSharples2- propanolGlycidols Mediatedpropionate-based stereotetradAlMe 3methodstereoselective allylationspolyketide constructionepoxidationaldehyde oxidation levelAsymmetric Allylationcatalyst-directed diastereoselectivity
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