期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 18, 页码 6816-6823出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo070978f
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资金
- NIGMS NIH HHS [R01 GM071492, GM 71492] Funding Source: Medline
The type 2 intramolecular N-acylazo Diels-Alder reaction provides a regio- and stereoselective synthesis of bicyclic 1,2-diazine systems. A new method for the generation of N-acylazo dienophiles with tetra-n-butylammonium periodate is reported. X-ray crystallographic analysis allowed the quantification of structural distortions of the nonplanar bridgehead olefin and lactam functionalities in 1,2-diazine cycloadducts 11 and 15. Caprolactams and enantholactams were formed by stereoselective bridgehead alkene reduction, a process that transfers stereochemistry from the bridgehead lactam nitrogen to the bridgehead carbon. The sequence of transformations offers a convenient route for the diastereoselective synthesis of medium-ring nitrogen heterocycles and 1,4-diamines.
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