Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 14, Pages 3987-3991Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700195
Keywords
asymmetric synthesis; deuterium labeling; hydride donors; oxindoles; reductive Heck reactions
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Funding
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF)
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Pd-catalyzed intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by reduction of C(sp(3))-Pd intermediate using diboron-water as a hydride source afforded enantioenriched 3,3-disubstituted oxindoles in high yields and enantioselectivities. When heavy water was used as a deuterium donor in combination with bis(catecholato)diboron (Cat(2)B(2)), deuterium was incorporated into the products with high synthetic efficiency. The ligand determined both the enantioselectivity of the reaction and the reaction pathways, thereby affording either hydroarylation (reductive Heck) or carboborylation products.
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