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Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes

หน่วยงาน Nanyang Technological University, Singapore

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ชื่อเรื่อง : Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes
นักวิจัย : Huang, Chuhui , Kothandaraman, Prasath , Koh, Bing Qin , Chan, Philip Wai Hong
คำค้น : DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds
หน่วยงาน : Nanyang Technological University, Singapore
ผู้ร่วมงาน : -
ปีพิมพ์ : 2555
อ้างอิง : Huang, C., Kothandaraman, P., Koh, B. Q., & Chan, P. W. H. (2012). Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes. Organic & Biomolecular Chemistry, 10(45), 9067-9078. , http://hdl.handle.net/10220/17219 , http://dx.doi.org/10.1039/c2ob26458g
ที่มา : -
ความเชี่ยวชาญ : -
ความสัมพันธ์ : Organic & biomolecular chemistry
ขอบเขตของเนื้อหา : -
บทคัดย่อ/คำอธิบาย :

The effects of starting material substitution patterns on reaction selectivity for the gold(I)-catalysed cycloisomerisations of aryl substituted 1,7-enynes were investigated. The results indicated the chemoselectivity of the reaction to be highly substrate and catalyst dependent. Either the piperidine or the tetrahydro-1H-azepine product was obtained in moderate to excellent yields depending on the steric and/or electronic nature of the substrate and the gold(I) catalyst. Overall, six-membered nitrogen ring formation was found to be favoured in reactions with 1,7-enyne derivatives containing a disubstituted alkene moiety or not bearing a sterically bulky substituent or a gold(I) catalyst with a pendant sterically unencumbered phosphine ligand. Formation of the seven-membered nitrogen heterocycle was observed in reactions where the substrate contained a tetrasubstituted alkene unit or a sterically demanding substituent.

บรรณานุกรม :
Huang, Chuhui , Kothandaraman, Prasath , Koh, Bing Qin , Chan, Philip Wai Hong . (2555). Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes.
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
Huang, Chuhui , Kothandaraman, Prasath , Koh, Bing Qin , Chan, Philip Wai Hong . 2555. "Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes".
    กรุงเทพมหานคร : Nanyang Technological University, Singapore.
Huang, Chuhui , Kothandaraman, Prasath , Koh, Bing Qin , Chan, Philip Wai Hong . "Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes."
    กรุงเทพมหานคร : Nanyang Technological University, Singapore, 2555. Print.
Huang, Chuhui , Kothandaraman, Prasath , Koh, Bing Qin , Chan, Philip Wai Hong . Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes. กรุงเทพมหานคร : Nanyang Technological University, Singapore; 2555.