Gold-Catalyzed Stereoselective Synthesis of Bicyclic Lactams and Ketones from N-Tosylynamidomethyl-Tethered Cyclohexenes

Chang Zhi Zhong, Po Ting Tung, Tsung Han Chao, Ming Chang P. Yeh

研究成果: 雜誌貢獻文章同行評審

10 引文 斯高帕斯(Scopus)

摘要

Six-membered ring 3-enynamides underwent cycloisomerization in the presence of a catalytic amount of a gold(I) complex delivering mainly 4-azatricyclo[4.3.1.03,10]dec-2-ene derivatives and dibenz[cd,f]indole derivatives as the minor products under mild reaction conditions. Upon exposure to air, most aryl-substituted azatricycles led to bicyclic γ-lactams, while the ortho-tolyl- or alkyl-substituted azatricycles provided the corresponding bicyclic γ-lactams after oxidation with osmium tetraoxide and N-methylmorpholine-N-oxide. Under acidic conditions, the ortho-tolyl- or alkyl-substituted azatricycles were further transformed into 5-N-tosylaminomethyl-tethered bicyclo[4.2.0]octan-7-ones. The gold(I)-catalyzed tandem cycloisomerization/oxidation reaction also provided a new route for the synthesis of bridged bicyclic δ-lactams from six-membered ring 4-enynamides. The mild reaction conditions allowed the synthesis of a range of bicyclic γ- and δ-lactams and N-tosylaminomethyl-tethered bicyclo[4.2.0]octan-7-ones with high diastereoselectivities.

原文英語
頁(從 - 到)481-501
頁數21
期刊Journal of Organic Chemistry
82
發行號1
DOIs
出版狀態已發佈 - 2017 一月 6

ASJC Scopus subject areas

  • Organic Chemistry

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