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From Palladium to Bronsted Acid Catalysis: Highly Enantioselective Regiodivergent Addition of Alkoxyallenes to Pyrazolones
Department苏州研究院
Zhou H(周慧)1,2; Wei, Zhao1,2; Zhang JL(张金龙)1; Yang HM(杨化萌)1; Xia CG(夏春谷)1; Jiang GX(蒋高喜)1; Jiang GX(蒋高喜)
The second departmentosso国家重点实验室
2017
Source PublicationAngewandte Chemie International Edition
ISSN1433-7851
Volume56Issue:4Pages:1077-1081
Abstract

A highly enantioselective regiodivergent addition of alkoxyallenes to pyrazolones was developed to afford multiply functionalized alkylated products bearing a quaternary carbon stereocenter in high yields with excellent stereoselectivities. One approach is enabled by palladium catalysis, thus leading to branched allylic pyrazol-5-ones under mild reaction conditions. The other is catalyzed by a chiral Brønsted acid to give linear products exclusively. Moreover, the usefulness of this new method was highlighted by converting the allylic products into other interesting multifunctionalized pyrazolone derivatives which would be of great potential for the exploitation of pharmaceutically important molecules.

KeywordAllenes Allylic Compounds Bronsted Acids Heterocycles Palladium
Subject Area物理化学与绿色催化
DOI10.1002/anie.201610473
Funding OrganizationHundred Talent Program of Chinese Academy of Sciences (CAS);the National Natural Science Foundation of China (21202175;21602231);the Natural Science Foundation of Jiangsu (BK20160396)
Indexed BySCI
If11.994
Language英语
Funding Project均相催化研究组
compositor第一作者单位
Citation statistics
Cited Times:69[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.licp.cn/handle/362003/21478
Collection苏州研究院
羰基合成与选择氧化国家重点实验室(OSSO)
Corresponding AuthorJiang GX(蒋高喜)
Affiliation1.Chinese Acad Sci, LICP, Suzhou Res Inst LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Zhou H,Wei, Zhao,Zhang JL,et al. From Palladium to Bronsted Acid Catalysis: Highly Enantioselective Regiodivergent Addition of Alkoxyallenes to Pyrazolones[J]. Angewandte Chemie International Edition,2017,56(4):1077-1081.
APA Zhou H.,Wei, Zhao.,Zhang JL.,Yang HM.,Xia CG.,...&蒋高喜.(2017).From Palladium to Bronsted Acid Catalysis: Highly Enantioselective Regiodivergent Addition of Alkoxyallenes to Pyrazolones.Angewandte Chemie International Edition,56(4),1077-1081.
MLA Zhou H,et al."From Palladium to Bronsted Acid Catalysis: Highly Enantioselective Regiodivergent Addition of Alkoxyallenes to Pyrazolones".Angewandte Chemie International Edition 56.4(2017):1077-1081.
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