Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C-H Activation/Carbene Insertion/Lossen Rearrangement Sequence

doi:10.1002/anie.201906589

	Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C-H Activation/Carbene Insertion/Lossen Rearrangement Sequence
	Ma, Biao 1; Wu, Peng 3; Wang, Xing 1; Wang, Zhengyu 1; Lin, Hai-Xia 3; Dai, Hui-Xiong 1,2
刊名	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
	2019-08-07
页码	6
关键词	C-H activation Lossen rearrangement olefins oxindoles rhodium catalysis
ISSN号	1433-7851
DOI	10.1002/anie.201906589
通讯作者	Dai, Hui-Xiong(hxdai@simm.ac.cn)
英文摘要	A rhodium(III)-catalyzed domino annulation of simple olefins with diazo oxindoles to give spirooxindole pyrrolone products is described. This reaction can be formally viewed as the result of an anomalous tandem C-H activation, carbene insertion, Lossen rearrangement, and a nucleophilic addition process. The potential utility of this reaction was further demonstrated by the late-stage diversification of drug molecules.
资助项目	Shanghai Institute of Materia Medica ; Chinese Academy of Sciences[CASIMM 0120163006] ; NSFC[21472211] ; NSFC[21502212] ; NSFC[21772211] ; Youth Innovation Promotion Association CAS[2014229] ; Youth Innovation Promotion Association CAS[2018293] ; Institutes for Drug Discovery and Development ; Science and Technology Commission of Shanghai Municipality[17JC1405000] ; Program of Shanghai Academic Research Leader[19XD1424600] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006] ; State Key Laboratory of Natural and Biomimetic Drugs
WOS关键词	ALDOSE REDUCTASE INHIBITORS ; MAMMALIAN-CELL CYCLE ; BOND FUNCTIONALIZATION ; ASYMMETRIC-SYNTHESIS ; SPIROTRYPROSTATIN B ; ALKYLATION ; DISCOVERY ; POTENT ; ARYL ; SPIROCYCLIZATION
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000480141000001
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/288866]
专题	中国科学院上海药物研究所
通讯作者	Dai, Hui-Xiong
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China 2.Peking Univ, Stake Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China 3.Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China
推荐引用方式 GB/T 7714	Ma, Biao,Wu, Peng,Wang, Xing,et al. Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C-H Activation/Carbene Insertion/Lossen Rearrangement Sequence[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2019:6.
APA	Ma, Biao,Wu, Peng,Wang, Xing,Wang, Zhengyu,Lin, Hai-Xia,&Dai, Hui-Xiong.(2019).Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C-H Activation/Carbene Insertion/Lossen Rearrangement Sequence.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,6.
MLA	Ma, Biao,et al."Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C-H Activation/Carbene Insertion/Lossen Rearrangement Sequence".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019):6.