Stereoselective synthesis of hexahydroindoles and octahydrocyclohepta[b]pyrroles via gold(I)-catalyzed intramolecular 1,4-hydroamination of cyclic 1,3-dienes

Ming Chang P. Yeh*, Hui Fen Pai, Zao Jun Lin, Bo Ren Lee

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

42 引文 斯高帕斯(Scopus)

摘要

The gold(I)-catalyzed intramolecular hydroamination of cyclohexa-1,3-dienes bearing an arylsulfonamide at the C-5 position proceeds in a 1,4-addition manner to afford hexahydroindole derivatives in a diastereoselective fashion and in good yields, whereas octahydrocyclohepta[b]pyrrole derivatives can be obtained from seven-membered ring substrates under the same reaction conditions. Coordination of the gold(I) species to the 1,3-diene at the double bond adjacent to the arylsulfonamide tether gave an η2-alkene gold complex. The anti-attack of the sulfonamide to the η2-alkene gold complex at the terminal position of the 1,3-diene resulted in the formation of the fused bicyclic ring with a newly formed Au-C bond at the allylic position. Allylic rearrangement of the η1-allylgold complex followed by protodemetalation provided the fused heterobicyclic skeletons and regenerated the catalyst.

原文英語
頁(從 - 到)4789-4794
頁數6
期刊Tetrahedron
65
發行號25
DOIs
出版狀態已發佈 - 2009 6月 20

ASJC Scopus subject areas

  • 生物化學
  • 藥物發現
  • 有機化學

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