Palladium(II)-Catalyzed Highly Enantioselective C–H Arylation of Cyclopropylmethylamines
2015
Chan, Kelvin S. L. | Fu, Hai-Yan | Yu, Jin-Quan
C–H arylation via a Pd(II)/Pd(IV) catalytic cycle has been one of the most extensively studied C–H activation reactions since the 1990s. Despite the rapid development of this reaction in the past two decades, an enantioselective version has not been reported to date. Herein, we report a Pd(II)-catalyzed highly enantioselective (up to 99.5% ee) arylation of cyclopropyl C–H bonds with aryl iodides using mono-N-protected amino acid (MPAA) ligands, providing a new route for the preparation of chiral cis-aryl-cyclopropylmethylamines. The enantiocontrol is also shown to override the diastereoselectivity of chiral substrates.
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