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Ring‐Opening Lithiation–Borylation of 2‐Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters
- Source :
- Nandakumar, M, Rubial, B, Noble, A, Myers, E L & Aggarwal, V K 2020, ' Ring-Opening Lithiation–Borylation of 2-Trifluoromethyl Oxirane : A Route to Versatile Tertiary Trifluoromethyl Boronic Esters ', Angewandte Chemie-International Edition, vol. 59, no. 3, pp. 1187-1191 . https://doi.org/10.1002/anie.201912797
- Publication Year :
- 2019
- Publisher :
- Wiley, 2019.
-
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.
- Subjects :
- lithiation–borylation
Trifluoromethyl
trifluoromethyl
Chemistry
010405 organic chemistry
chemistry.chemical_element
General Chemistry
General Medicine
Ring (chemistry)
010402 general chemistry
Borylation
Combinatorial chemistry
01 natural sciences
Catalysis
Stereocenter
stereospecific synthesis
0104 chemical sciences
chemistry.chemical_compound
quaternary center
Stereospecificity
fluorine
Fluorine
Subjects
Details
- ISSN :
- 15213757 and 00448249
- Volume :
- 132
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie
- Accession number :
- edsair.doi.dedup.....57b7e761fe1663c8481e657cd0f92988