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- W2952213547 abstract "Chiral silylated pyrrolidine catalysts are obtained in high yield and enantioselectivity by sparteine-mediated lithiation of N-Boc-pyrrolidine and addition to silyl fluoride electrophiles. The activity and enantioselectivity of a new tert-butyldiphenylsilylpyrrolidine catalyst has been demonstrated for various asymmetric Michael reactions at 5 mol % catalyst loading and affords up to 99% ee for asymmetric Michael reactions with aldehydes and nitro-olefins. Acetaldehyde donors proceed with yields up to 77% and enantioselectivities up to 96% ee, avoiding common side reactions that often lower yields. Insight into the mechanism of pyrrolidine-based catalysts is provided by demonstrating ESI mass spectrometry evidence for activation of a nitro acceptor by formation of a hydrogen-bonding adduct with the catalyst amine. Analysis of reaction intermediates using mass spectrometry provides evidence that the pyrrolidine catalyst also plays a role in activating nitro-olefins through hydrogen-bonding." @default.
- W2952213547 created "2019-06-27" @default.
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- W2952213547 creator A5051684238 @default.
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- W2952213547 date "2011-08-01" @default.
- W2952213547 modified "2023-10-09" @default.
- W2952213547 title "Silyl Fluoride Electrophiles for the Enantioselective Synthesis of Silylated Pyrrolidine Catalysts" @default.
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- W2952213547 doi "https://doi.org/10.1021/jo200991q" @default.
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