Gold-Catalyzed Intermolecular Reactions of Propiolic Acids with Alkenes: [4+2] Annulation and Enyne Cross Metathesis
- Title
- Gold-Catalyzed Intermolecular Reactions of Propiolic Acids with Alkenes: [4+2] Annulation and Enyne Cross Metathesis
- Author
- 신승훈
- Issue Date
- 2012-01
- Publisher
- AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 권: 134, 호: 1, 페이지: 208-211
- Abstract
- 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.
- URI
- https://pubs.acs.org/doi/abs/10.1021/ja210792ehttp://hdl.handle.net/20.500.11754/37525
- ISSN
- 0002-7863
- DOI
- 10.1021/ja210792e
- Appears in Collections:
- COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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