期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 1, 页码 208-211出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja210792e
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资金
- National Research Foundation of Korea [NRF-2009-0080741, NRF-2011-0023686]
- BK21 program
- Seoul Science Foundation
- NSFC [20825205]
- National Research Foundation of Korea [2011-0023686, 2009-0080741] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
A gold-catalyzed intermolecular reaction of propiolic acids with alkenes led to a [4 + 2] annulation or enyne cross metathesis. The [4 + 2] annulation proceeds with net cis-addition with respect to alkenes and provides an expedient route to alpha,beta-unsaturated delta-lactones, for which preliminary asymmetric reactions were also demonstrated. For 1,2-disubstituted alkenes, unprecedented enyne cross metathesis occurred to give I,3-dienes in a completely stereospecific fashion. DFT calculations and experiments indicated that the cyclobutene derivatives are not viable intermediates and that the steric interactions during concerted sigma-bond rearrangements are responsible for the observed unique stereospecificity.
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