Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 9, Pages 4357-4365Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400365e
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Funding
- National Basic Research Program of China (973 Program) [2010CB833300]
- National Natural Science Foundation of China [20923005, 21025209, 21121062]
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This paper describes a combined theoretical and experimental investigation into the acid-catalyzed migration of spiroindolenines to the corresponding fused cyclic products. It is suggested that the three-center-two-electron-type transition state is the crucial reason accounting for the highly stereoselective phenomenon. Further studies demonstrated that the electronic property of the migratory group as well as the ring size may have a major influence on the reaction profile of the migration process. Some predictions based on the computational results were supported by additional experiments.
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