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Issue 16, 1999
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Asymmetric protonation of lithium enolate using 5-substituted pyrrolidin-2-one as a chiral proton source

Abstract

Asymmetric protonation of the lithium enolate moiety of a 2-substituted α-tetralone (3,4-dihydronaphthalen-1(2H )-one) was examined using 5-substituted pyrrolidin-2-ones as chiral proton sources. Among the three types of pyrrolidin-2-ones bearing either a hydroxymethyl group or steric bulk or a chelation site at the 5-position, the pyrrolidin-2-ones bearing steric bulk gave the enantiomerically enriched α-tetralone derivative in up to 72% ee.

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Article type: Paper
DOI: 10.1039/A901581G
Citation: J. Chem. Soc., Perkin Trans. 1, 1999, 2377-2381
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    Asymmetric protonation of lithium enolate using 5-substituted pyrrolidin-2-one as a chiral proton source

    H. Fujihara and K. Tomioka, J. Chem. Soc., Perkin Trans. 1, 1999, 2377
    DOI: 10.1039/A901581G

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