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• W2094216461 abstract "A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic alcohols. Formation of a benzylic mesylate (which is not isolated), followed by treatment with an arylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-coupling product in high ee and good yield. A wide array of functional groups (e.g., an aryl iodide, a thiophene, and an N-Boc-indole) are compatible with the mild reaction conditions. This method has been applied to a gram-scale synthesis of a precursor to Zoloft." @default.
• W2094216461 created "2016-06-24" @default.
• W2094216461 creator A5016642366 @default.
• W2094216461 creator A5018387851 @default.
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• W2094216461 date "2013-10-28" @default.
• W2094216461 modified "2023-10-10" @default.
• W2094216461 title "Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes" @default.
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• W2094216461 doi "https://doi.org/10.1021/ja408561b" @default.
• W2094216461 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3869004" @default.
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