期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 5, 页码 2496-2500出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo202252y
关键词
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资金
- NSF [CHE-1112397]
- Welch Foundation [A-1280]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1112397] Funding Source: National Science Foundation
An improved, tandem acid activation/aldol-lactonization process is described. This more practical protocol shortens reaction times for the construction of bicyclic beta-lactones from ketoacids and implements the use of commercially available reagents p-toluenesulfonyl chloride (p-TsC1) as activator and 4-dimethylaminopyridine (4-DMAP) as nucleophllic promoter (Lewis base). Substrates with beta-substituents, with respect to the carboxylic acid, consistently showed excellent levels of diastereoselectivity during the bis-cyclization event.
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