We have developed a chiral phosphoric acid-catalyzed
enantioselective
Friedel–Crafts alkylation reaction between pyrroles and indolylmethanols.
Wide substrate scope was observed, and a chiral all-carbon quaternary
center was constructed at the 3 position of indoles in high yields
with high to excellent enantioselectivities (up to 99% ee).
Desymmetrization is an essential
method for the synthesis
of chiral
compounds, particularly chiral biaryls. We have developed an enantioselective
synthesis of axially chiral biaryls by desymmetrization using C(sp3)–H activation catalyzed by chiral palladium phosphate.
Mechanistic studies show that C–H activation is the rate- and
enantiomer-determining step. To the best of our knowledge, this is
the first report of asymmetric desymmetrization of axially chiral
compounds by C(sp3)–H activation.
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