期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 6, 页码 2731-2735出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo3026548
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资金
- National Science Foundation [CHE1011788]
- Arkansas Biosciences Institute
- NIH [P30 GM 103450]
- Swiss National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1011788] Funding Source: National Science Foundation
A library of iridium and rhodium phosphine catalysts have been screened for the double-asymmetric hydrogenation of 2,6-di-(1-phenylethenyl)-4-methylaniline to produce the C-2-symmetric aniline precursor of the N-heterocyclic carbenoid CuIPhEt. The best catalyst produced the desired enantiomer in 98.6% selectivity. This rare example of a highly selective hydrogenation of a 1,1-diaryl olefin enables a four-step asymmetric synthesis of the C-2-symmetric phenylethyl imidazolium ion (IPhEt) from p-toluidine and phenylacetylene and its conversion to the hydrosilylation catalyst CuIPhEt.
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