Rh-II-Catalyzed Reaction of alpha-Diazocarbonyl Compounds Bearing   beta-Trichloroacetylamino Substituent: C-H Insertion versus 1,2-H Shift

doi:10.1002/asia.200900352

CORC > 北京大学 > 化学与分子工程学院

	Rh-II-Catalyzed Reaction of alpha-Diazocarbonyl Compounds Bearing beta-Trichloroacetylamino Substituent: C-H Insertion versus 1,2-H Shift
	Zhang, Zhenhua ; Shi, Weifeng ; Zhang, Jian ; Zhang, Bo ; Liu, Bingge ; Liu, Yiyang ; Fan, Bo ; Xiao, Fengping ; Xu, Feng ; Wang, Jianbo
刊名	chemistry an asian journal
	2010
关键词	carbenes diazo compounds hydrides insertion substituent effects DIAZO CARBONYL-COMPOUNDS 1ST ENANTIOSPECIFIC SYNTHESIS ENANTIOSELECTIVE SYNTHESIS CYCLOPENTANE CONSTRUCTION ORGANIC-SYNTHESIS DIRHODIUM TETRACARBOXYLATE CARBENOID REACTIONS HYDROXY ESTERS RING EXPANSION ALLYLIC AMINES
DOI	10.1002/asia.200900352
英文摘要	The Rh-II-carbene reaction is dramatically affected by the neighboring substituents. If the neighboring substituent is an OH group, a1,2-H shift is the exclusive pathway. If it is an OAc group, a 1,2-acetoxy migration is observed. If it is p-toluenesulfonyl group, 1,3 and 1,5-C-H insertion are the major pathways, and the 1,2-H shift is completely suppressed. If the adjacent substituent is a trichloroacetyl amino group, 1.,5-C-H insertion competes with the 1,2-hydride shift, and no 1,3-C H insertion can be observed. Both electronic and steric factors are responsible for the switching of the Rh-II-carbene reaction pathway. The highly stereoselective 1,5-C-H insertions in Rh-II-catalyzed reaction of alpha-diazocarbonyl compounds, bearing beta-trichloroacetylamino substituent, can be utilized as a novel way to synthesize five-membered cyclic beta-amino acid derivatives.; http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000277724800012&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701 ; Chemistry, Multidisciplinary; SCI(E); PubMed; 11; ARTICLE; 5; 1112-1119; 5
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/197535]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Zhang, Zhenhua,Shi, Weifeng,Zhang, Jian,et al. Rh-II-Catalyzed Reaction of alpha-Diazocarbonyl Compounds Bearing beta-Trichloroacetylamino Substituent: C-H Insertion versus 1,2-H Shift[J]. chemistry an asian journal,2010.
APA	Zhang, Zhenhua.,Shi, Weifeng.,Zhang, Jian.,Zhang, Bo.,Liu, Bingge.,...&Wang, Jianbo.(2010).Rh-II-Catalyzed Reaction of alpha-Diazocarbonyl Compounds Bearing beta-Trichloroacetylamino Substituent: C-H Insertion versus 1,2-H Shift.chemistry an asian journal.
MLA	Zhang, Zhenhua,et al."Rh-II-Catalyzed Reaction of alpha-Diazocarbonyl Compounds Bearing beta-Trichloroacetylamino Substituent: C-H Insertion versus 1,2-H Shift".chemistry an asian journal (2010).