Lewis Acid Catalyzed Cyclization of Glycals/2-Deoxy-D-ribose with Arylamines: Additional Findings on Product Structure and Reaction Diastereoselectivity

doi:10.1021/jo2015483

	Lewis Acid Catalyzed Cyclization of Glycals/2-Deoxy-D-ribose with Arylamines: Additional Findings on Product Structure and Reaction Diastereoselectivity
	Du, Chengtang 1,2; Li, Fulong 2,3; Zhang, Xuefeng 2; Hu, Wenxiang 1; Yao, Qizheng 3; Zhang, Ao1
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2011-11-04
卷号	76 期号:21 页码:8833-8839
ISSN号	0022-3263
DOI	10.1021/jo2015483
文献子类	Article
英文摘要	The cyclization reactions of arylamines with 2-deoxy-D-ribose or glycals were reinvestigated in the current report. In the montmorillonite KSF- or InCl3-initiated reactions of 2-deoxy-D-ribose with arylamines, a pair of diastereomeric tetrahydro-2H-pyran-fused tetrahydroquinolines was obtained in a nearly 1:1 ratio where the structure of one diastereomer was incorrectly assigned in the literature. Meanwhile, the diastereoselectivity in InBr3-catalyzed cyclization of glycals with arylamines was also incorrectly reported previously. It was found that high diastereomeric selectivity was achieved only when a CS substituted glycal was used; otherwise, a pair of diastereomers was obtained in moderate yield with 1:1 diastereomeric ratio. Furthermore, tetrahydrofuran-fused tetrahydroquinolines 5b and 5b' were also prepared successfully by using TBDPS-protected ribose as the glycal precursor and montmorillonite KSF as the activator.
资助项目	Chinese National Science Foundation[81072528] ; Shanghai Commission of Science and Technology[10410702600] ; Shanghai Commission of Science and Technology[10JC1417100] ; Shanghai Commission of Science and Technology[10dz1910104] ; National Science & Technology Major Project on "Key New Drug Creation and Manufacturing Program"[2012ZX09101] ; National Science & Technology Major Project on "Key New Drug Creation and Manufacturing Program"[2009ZX09301-001] ; National Science & Technology Major Project on "Key New Drug Creation and Manufacturing Program"[2009ZX09103-062] ; Key Laboratory of Pesticide & Chemical Biology, Central China Normal University[201005A02]
WOS关键词	ARYL AMINES ; TETRAHYDROQUINOLINES ; DERIVATIVES ; GLYCALS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000296206400025
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/278339]
专题	药物化学研究室
通讯作者	Hu, Wenxiang
作者单位	1.Capital Normal Univ, Dept Chem, Beijing 100048, Peoples R China; 2.SIMM, SOMCL, Shanghai 201203, Peoples R China; 3.China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Peoples R China
推荐引用方式 GB/T 7714	Du, Chengtang,Li, Fulong,Zhang, Xuefeng,et al. Lewis Acid Catalyzed Cyclization of Glycals/2-Deoxy-D-ribose with Arylamines: Additional Findings on Product Structure and Reaction Diastereoselectivity[J]. JOURNAL OF ORGANIC CHEMISTRY,2011,76(21):8833-8839.
APA	Du, Chengtang,Li, Fulong,Zhang, Xuefeng,Hu, Wenxiang,Yao, Qizheng,&Zhang, Ao.(2011).Lewis Acid Catalyzed Cyclization of Glycals/2-Deoxy-D-ribose with Arylamines: Additional Findings on Product Structure and Reaction Diastereoselectivity.JOURNAL OF ORGANIC CHEMISTRY,76(21),8833-8839.
MLA	Du, Chengtang,et al."Lewis Acid Catalyzed Cyclization of Glycals/2-Deoxy-D-ribose with Arylamines: Additional Findings on Product Structure and Reaction Diastereoselectivity".JOURNAL OF ORGANIC CHEMISTRY 76.21(2011):8833-8839.