3 years ago

Asymmetric Cycloisomerization of o-Alkenyl-N-Methylanilines to Indolines by Iridium-Catalyzed C(sp3)−H Addition to Carbon–Carbon Double Bonds

Asymmetric Cycloisomerization of o-Alkenyl-N-Methylanilines to Indolines by Iridium-Catalyzed C(sp3)−H Addition to Carbon–Carbon Double Bonds
Michinori Suginome, Toshimichi Ohmura, Takeru Torigoe
Highly enantioselective cycloisomerization of N-methylanilines, bearing o-alkenyl groups, into indolines is established. An iridium catalyst bearing a bidentate chiral diphosphine effectively promotes the intramolecular addition of the C(sp3)−H bond across a carbon–carbon double bond in a highly enantioselective fashion. The reaction gives indolines bearing a quaternary stereogenic carbon center at the 3-position. The reaction mechanism involves rate-determining oxidative addition of the N-methyl C−H bond, followed by intramolecular carboiridation and subsequent reductive elimination. Build a bridge: Highly enantioselective cycloisomerization of N-methylanilines, bearing o-alkenyl groups, into indolines was established. An iridium catalyst bearing a bidentate chiral diphosphine effectively promotes the intramolecular addition of the C(sp3)−H bond across a C=C bond in an enantioselective fashion. The reaction gives indolines bearing a quaternary stereogenic carbon center at the 3-position.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708578

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