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Ring-Opening Lithiation–Borylation of 2-Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters

Research output: Contribution to journalArticle (Academic Journal)

Original languageEnglish
Pages (from-to)1187-1191
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number3
Early online date11 Nov 2019
DOIs
DateAccepted/In press - 11 Nov 2019
DateE-pub ahead of print - 11 Nov 2019
DatePublished (current) - 13 Jan 2020

Abstract

Stereogenic trifluoromethyl-substituted carbon centers are highly sought-after moieties in pharmaceutical and agrochemical discovery. Here, we show that lithiation–borylation reactions of 2-trifluoromethyl oxirane give densely functionalized and highly versatile trifluoromethyl-substituted α-tertiary boronic esters. The intermediate boronate complexes undergo the desired 1,2-rearrangement of the carbon-based group with complete retentive stereospecificity, a process that was only observed in non-polar solvents in the presence of TESOTf. Although the trifluoromethyl group adversely affects subsequent transformations of the α-boryl group, Zweifel olefinations provide trifluoromethyl-bearing quaternary stereocenters substituted with alkenes, alkynes and ketones.

    Research areas

  • fluorine, lithiation–borylation, quaternary center, stereospecific synthesis, trifluoromethyl

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  • Full-text PDF (accepted author manuscript)

    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Wiley at https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201912797. Please refer to any applicable terms of use of the publisher.

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