AgAsF<sub>6</sub>/Sm(OTf)<sub>3</sub> Promoted Reversal of Enantioselectivity for the Asymmetric Friedel−Crafts Alkylations of Indoles with β,γ-Unsaturated α-Ketoesters
Organic LettersPublished 25 November 2009
Yanling Liu, Deju Shang, Xin Zhou, Yin Zhu, Lili Lin, Xiaohua Liu
Citations104
SJR quartileQ1
SJR score1.24
SNIP1.03
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TL;DR
The first example of central metal controlled reversal of enantioselectivity in asymmetric Friedel-Crafts alkylation of indoles and beta,gamma-unsaturated alpha-ketoesters has been developed.
Abstract
The first example of central metal controlled reversal of enantioselectivity in asymmetric Friedel-Crafts alkylation of indoles and beta,gamma-unsaturated alpha-ketoesters has been developed. Using the same chiral starting material derived N,N'-dioxides 1a and 1b as ligands, various indole esters 4 were obtained in good to excellent yields and enantioselectivities. The reaction also featured mild reaction conditions and remarkably low catalyst loading (down to 0.01 mol %).
Keywords
ChemistryPharmacology, Toxicology and Pharmaceutics
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