Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 51, Pages 16028-16031Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b11625
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- EPFL
- Swiss National Science Foundation (SNSF)
- Swiss National Centres of Competence in Research (NCCR-Chemical Biology)
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Intrarmolecular asymmetric carbopalladation of N-aryl acrylamides followed by intermolecular trapping of the resulting sigma-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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