Stereospecific cross-coupling reactions of aryl-substituted tetrahydrofurans, tetrahydropyrans, and lactones

Emily J. Tollefson, David D. Dawson, Charlotte A. Osborne, Elizabeth R. Jarvo

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

The stereospecific ring-opening of O-heterocycles to provide acyclic alcohols and carboxylic acids with controlled formation of a new C-C bond is reported. These reactions provide new methods for synthesis of acyclic polyketide analogs with complex stereochemical arrays. Stereoselective synthesis of the cyclic template is utilized to control relative configuration; subsequent stereospecific nickel-catalyzed ring-opening affords the acyclic product. Aryl-substituted tetrahydrofurans and tetrahydropyrans undergo nickel-catalyzed Kumada-type coupling with a range of Grignard reagents to furnish acyclic alcohols with high diastereoselectivity. Enantioenriched lactones undergo Negishi-type cross-coupling with dimethylzinc to afford enantioenriched carboxylic acids. Application in a two-step enantioselective synthesis of an antidyslipidemia agent is demonstrated.

Original languageEnglish (US)
Pages (from-to)14951-14958
Number of pages8
JournalJournal of the American Chemical Society
Volume136
Issue number42
DOIs
StatePublished - Oct 22 2014

Bibliographical note

Publisher Copyright:
© 2014 American Chemical Society.

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