期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 28, 页码 12394-12399出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c04725
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资金
- National Natural Science Foundation of China [21625204, 21790332, 21532003, 21971119]
- 111 project of the Ministry of Education of China [B06005]
- National Program for Special Support of Eminent Professionals
- National Science Foundation of the USA [CHE-176328]
- National Institute of Health [T32GM008496]
Catalytic enantioselection usually depends on differences in steric interactions between prochiral substrates and a chiral catalyst. We have discovered a carbene Si-H insertion in which the enantioselectivity depends primarily on the electronic characteristics of the carbene substrate, and the log(er) values are linearly related to Hammett parameters. A new class of chiral tetraphosphate dirhodium catalysts was developed; it shows excellent activity and enantioselectivity for the insertion of diarylcarbenes into the Si-H bond of silanes. Computational and mechanistic studies show how the electronic differences between the two aryls of the carbene lead to differences in energies of the diastereomeric transition states. This study provides a new strategy for asymmetric catalysis exploiting the electronic properties of the substrates.
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