期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 14, 页码 3987-3991出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700195
关键词
asymmetric synthesis; deuterium labeling; hydride donors; oxindoles; reductive Heck reactions
资金
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF)
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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