期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 17, 页码 5984-5993出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo1013383
关键词
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资金
- Japan Society for the Promotion of Sciences [21590124, 21790025]
- Grants-in-Aid for Scientific Research [21790025, 21590124] Funding Source: KAKEN
The atropisomeric enantiomers of 7-, 8-, and 9-membered-ring dibenzolactams were separated by using chiral H PLC, and their stereochemistries were clarified by using X-ray crystallographic analysis. The atropisomers showed high stereochemical stability with the 8-membered ring being the most stable. In 7- and 8-membered dibenzolactams, highly stereoselective C7-methylation proceeded from the lower side of the ring to provide the products with a C7-methyl group in the pseudoaxial orientation, which converted to thermodynamically more stable isomers with the pseudoequatorial C7-methyl group. In 9-membered dibenzolactam, C7-methylation occurred from the opposite (upper) side of the ring to provide a thermodynamically stable product with the pseudoequatorial C7-methyl group.
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