Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C–H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole

Intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by intermolecular trapping of the resulting σ-C(sp3)−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.


Published in:
Journal of the American Chemical Society, 137, 51, 16028-16031
Year:
2015
Publisher:
American Chemical Society
ISSN:
1520-5126
Laboratories:




 Record created 2016-01-04, last modified 2018-09-13


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