期刊
CHEMICAL SCIENCE
卷 10, 期 19, 页码 5176-5182出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc00633h
关键词
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资金
- National Science Foundation [CHE-1800012]
- ACS Petroleum Research Fund [56575-DNI1]
- Duke University
- Duke Chemistry Department
We describe the development of Pd-PHOX-catalysed enantioselective couplings of internal dienes with malononitrile and other activated C-pronucleophiles. Reactions are dramatically accelerated by the addition of Et3N$ HBArF 4 as a Bronsted acid co-catalyst, enabling a suite of products bearing a variety of alkyl substituents at the stereogenic carbon to be prepared. A series of mechanism-oriented experiments reveal key aspects of the catalytic cycle and the importance of the non-coordinating BArF 4 counterion in not only promoting reactions of internal dienes but also additions of previously unreactive nucleophiles towards terminal dienes.
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