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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Controllable enantioselective Friedel-Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo-C3-symmetric trisoxazoline copperII complexes.

Pseudo-C(3)-symmetric trisoxazoline copper(II) complexes prove to be excellent catalysts in the Friedel-Crafts alkylation of indoles with alkylidene malonates. The absolute stereochemistry of this reaction is shown to be dependent on the solvent. Reactions in isobutyl alcohol afford the Friedel-Crafts alkylation adducts in excellent yields and with up to +98% ee. In 1,1,2,2-tetrachloroethane (TTCE), however, the opposite enantiomers of the products are obtained in good yields with up to -89% ee. Water tolerance of chiral catalyst trisoxazoline 2a/Cu(OTf)(2) is examined, and it is found that the addition of up to 200 equiv of water relative to catalyst in isobutyl alcohol has almost no effect on enantioselectivity but slows down the reaction. The reaction scope is studied as well. The roles of alcohol as the solvent to accelerate the reaction are discussed. The stereochemical models of asymmetric induction for reactions both in isobutyl alcohol and in TTCE are also developed.[1]


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