Phosphine-catalyzed [3+2] annulation of 2-aminoacrylates with allenoates and mechanistic studies

Wu, Xiao-Yun1,2; Gui, Hou-Ze1,2; Jangra, Harish3; Wei, Yin4; Zipse, Hendrik3; Shi, Min1,2,4,5

2020-06-21

10.1039/d0cy00092b

Catalysis Science & Technology   影响因子和分区

2044-4753

2044-4761

A convenient and efficient strategy for the synthesis of 3-pyrrolines containing an amino quaternary stereogenic centerviaphosphine-catalyzed formal [3 + 2] annulation of 2-aminoacrylates with allenoates is disclosed. A wide range of substrates underwent this reaction smoothly, affording a series of 3-pyrrolines in good to excellent yields, and it could be extended to a gram-scale reaction. The kinetic profiles and the calculated methyl anion affinity (MAA) values were employed to explain the reactivities of different allenoates used in the reaction, which provides deep understanding for the catalytic mechanism of this type of reaction.

SCI ; EI

英语

通讯

Strategic Priority Research Program of the Chinese Academy of Sciences[XDB20000000] ; National Natural Science Foundation of China[21572052][21421091][21772226][21772037][21861132014][91956115] ; Fundamental Research Funds for the Central Universities[222201717003] ; Deutsche Forschungsgemeinschaft (DFG)[ZI 436/19-1]

Chemistry

Chemistry, Physical

WOS:000543417300011

ROYAL SOC CHEMISTRY

20202808909932

Phosphorus compounds

Chemical Reactions:802.2

Web of Science

1.East China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China
2.East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China
3.Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13, D-81377 Munich, Germany
4.Chinese Acad Sci, State Key Lab Organomet Chem, Ctr Excellence Mol Synth, Univ Chinese Acad Sci,Shanghai Inst Organ Chem, 315 Lingling Rd, Shanghai 200032, Peoples R China
5.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518000, Guangdong, Peoples R China

Wu, Xiao-Yun,Gui, Hou-Ze,Jangra, Harish,et al. Phosphine-catalyzed [3+2] annulation of 2-aminoacrylates with allenoates and mechanistic studies[J]. Catalysis Science & Technology,2020,10(12):3959-3964.

Wu, Xiao-Yun,Gui, Hou-Ze,Jangra, Harish,Wei, Yin,Zipse, Hendrik,&Shi, Min.(2020).Phosphine-catalyzed [3+2] annulation of 2-aminoacrylates with allenoates and mechanistic studies.Catalysis Science & Technology,10(12),3959-3964.

Wu, Xiao-Yun,et al."Phosphine-catalyzed [3+2] annulation of 2-aminoacrylates with allenoates and mechanistic studies".Catalysis Science & Technology 10.12(2020):3959-3964.