Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C-H Bond Functionalization: Development and
Wangqing Kong1, Qian Wang1, Jieping Zhu1
1Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland.
Abstract:
Intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by intermolecular trapping of the resulting σ-C(sp(3))-Pd complex by azoles afforded 3,3-disubstituted oxindoles in good yields with excellent enantioselectivities. Two C-C bonds were created with concurrent formation of an all-carbon quaternary stereocenter. Oxadiazole substituted oxindoles were subsequently converted to pyrroloindolines by an unprecedented reductive cyclization protocol. The utility of this chemistry was illustrated by an enantioselective synthesis of (+)-esermethole.
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