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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

Original languageEnglish
Number of pages6
JournalAngewandte Chemie - International Edition
Early online date2 Dec 2019
DOIs
DateAccepted/In press - 11 Nov 2019
DateE-pub ahead of print (current) - 2 Dec 2019

Abstract

Stereogenic trifluoromethyl‐substituted carbon centres are highly sought‐after moieties in pharmaceutical and agrochemical discovery. Here, we show that lithiation–borylation reactions of 2‐trifluoromethyl oxirane give densely functionalised 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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    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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