Asymmetric Allylation of Glycidols Mediated by Allyl Acetate via Iridium-Catalyzed Hydrogen Transfer.

Author(s) Kim, S.Wook; Lee, W.; Krische, M.J.
Journal Org Lett
Date Published 2017 Feb 21
Abstract

Glycidols 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.

DOI 10.1021/acs.orglett.7b00343
ISSN 1523-7052
Citation Org Lett. 2017.

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