Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 14, Pages 6532-6553Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo501011u
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- European Social Fund under the Global Grant measure [VP1-3.1-SMM-07-K-01-002]
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Kabachnik-Fields reactions of various carbocyclic or heterocyclic acetylenic aldehydes together with subsequent Lewis acid catalyzed cyclizations have been studied. It was found that 5-exo-dig versus 6-endo-dig cyclization mode strongly depends on the structure of starting materials. Thus, nonaromatic acetylenic alpha-anilinomethylphosphonates underwent gold(III)-catalyzed or iodine-mediated 5-exo-dig cyclization to 1H-pyrrol-2-ylphosphonates. In contrast, electron-withdrawing heteroaromatic substrates formed 1,2-dihydropyridin-2-yl-phosphonate ring containing materials via an exclusive 6-endo-dig ring-closure process. The dual mode of cyclization is possible only for alpha-amino (2-alkynylphenyl)methylphosphonates containing a benzene ring.
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