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 |
卷 | 82 |
發行號 | 1 |
DOIs | |
出版狀態 | 已發佈 - 2017 1月 6 |
ASJC Scopus subject areas
- 有機化學
指紋
深入研究「Gold-Catalyzed Stereoselective Synthesis of Bicyclic Lactams and Ketones from N-Tosylynamidomethyl-Tethered Cyclohexenes」主題。共同形成了獨特的指紋。資料集
-
CCDC 1491130: Experimental Crystal Structure Determination
Zhong, C.-Z. (Creator), Tung, P.-T. (Creator), Chao, T.-H. (Creator) & Yeh, M.-C. P. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1m1mz8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1m1mz8&sid=DataCite
資料集: Dataset
-
CCDC 1497579: Experimental Crystal Structure Determination
Zhong, C.-Z. (Creator), Tung, P.-T. (Creator), Chao, T.-H. (Creator) & Yeh, M.-C. P. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1m8c08, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1m8c08&sid=DataCite
資料集: Dataset
-
CCDC 1491085: Experimental Crystal Structure Determination
Zhong, C.-Z. (Creator), Tung, P.-T. (Creator), Chao, T.-H. (Creator) & Yeh, M.-C. P. (Creator), Unknown Publisher, 2017
DOI: 10.5517/ccdc.csd.cc1m1ljs, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1m1ljs&sid=DataCite
資料集: Dataset