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- W2096643409 endingPage "3004" @default.
- W2096643409 startingPage "2996" @default.
- W2096643409 abstract "Abstract This article addresses the mechanistic features of asymmetric carbolithiation of β‐methylstyrenes. While often the presence of functional groups is required to obtain high enantioselectivities in carbolithiation reactions, simple β‐methylstyrene also gives high selectivities in (−)‐sparteine‐mediated addition of alkyl lithium compounds. Computational studies on the carbolithiation of β‐methylstyrene with (−)‐sparteine show that the observed selectivities are the result of repulsion effects in the diastereomeric transition states between the (−)‐sparteine ⋅ alkyl lithium adduct and the β‐methylstyrene, upon approximation of the two reactants. In contrast, for the ortho ‐amino β‐methylstyrene ( E )‐benzyl(2‐propenylphenyl)amine ( 4 ) X‐ray structure analyses of intermediate lithium amides indicate a carbolithiation mechanism in which one side of the double bond is shielded by the amide moiety, leaving only one side free for approach of the chiral alkyl lithium adduct." @default.
- W2096643409 created "2016-06-24" @default.
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- W2096643409 creator A5054638656 @default.
- W2096643409 creator A5084742564 @default.
- W2096643409 creator A5051471297 @default.
- W2096643409 date "2011-02-03" @default.
- W2096643409 modified "2023-10-18" @default.
- W2096643409 title "Mechanistic Insight into Stereoselective Carbolithiation" @default.
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