Asymmetric Functionalization of C–H Bonds
CHAPTER 6: Asymmetric Friedel–Crafts Alkylation Reactions
Published:30 Jul 2015
Special Collection: 2015 ebook collection , 2011-2015 organic chemistry subject collectionSeries: Catalysis Series
Q. Kang and S. You, in Asymmetric Functionalization of C–H Bonds, ed. S. You, The Royal Society of Chemistry, 2015, pp. 214-282.
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The asymmetric Friedel–Crafts (AFC) alkylation reaction is one of the most important approaches to the synthesis of optically pure organic compounds. Various catalytic systems, including well-defined organometallic complexes (Zn, Cu, Sc, etc.) and small organic molecules (chiral imidazolidinones, thioureas, prolinols, BINOL-derived phosphoric acids, etc.), have been successfully developed and applied in asymmetric Friedel–Crafts alkylation reactions. Remarkable levels of enantioselectivity have been achieved for electron-rich arenes such as indoles, pyrroles, and naphthols, and electrophiles such as carbonyl compounds, imines, α,β-unsaturated carbonyl compounds, and π-allyl metal species.