Type 2 intramolecular N-acylazo Diels-Alder reaction: regio- and stereoselective synthesis of bridgehead bicyclic 1,2-diazines |
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Authors: | Molina Claudia L Chow Chun P Shea Kenneth J |
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Affiliation: | Department of Chemistry, Natural Science II, University of California Irvine, Irvine, California 92697-2025, USA. |
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Abstract: | 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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