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

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.

SUBMITTER: Kim SW

PROVIDER: S-EPMC5651674 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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

Kim Seung Wook SW Lee Wonchul W Krische Michael J MJ

Organic letters 20170221 5

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 AlMe<sub>3</sub>-n-BuLi is used to prepare the propionate-based stereotetrad spanning C17-C23 of dictyostatin, illustrating how this method may be applied ...[more]

PMID: 28221810

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