期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 38, 页码 16486-16492出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c08319
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资金
- Swiss National Science Foundation [200021_188490]
- University of Geneva
- Ste'onal Science Foundation
- Swiss National Science Foundation (SNF) [200021_188490] Funding Source: Swiss National Science Foundation (SNF)
Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp(3)) nucleophiles, a highly regioselective 1,4-addition process is favored. The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. With use of a chiral ligand and imides as carbon nucleophiles, a 3,4-addition protocol was developed, enabling construction of two contiguous tertiary stereocenters in a single step with moderate to high levels of diastereocontrol and excellent enantiocontrol. Both methods operate under mild reaction conditions, display a broad scope, and show excellent functional group tolerance. The synthetic potential of the 3,4-hydroalkylation reaction was established via a series of postcatalytic modifications.
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