![2-Bromo-7-chloro-4H-pyrrolo[2,3-b]pyrazine structure](https://static.chemtradehub.com/structs/115/1150617-58-5-0b0a.webp "2-Bromo-7-chloro-4H-pyrrolo[2,3-b]pyrazine structure")
The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition
Literature Information
Publication Date
2016-10-08
DOI
10.1039/C6QO00512H
Impact Factor
5.281
Authors
Fu-Sheng He, Cong-Shan Li, Hua Deng, Xing Zheng, Zhong-Tao Yang, Wei-Ping Deng
View Original
Abstract
A highly efficient copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with β-phthaliminoacrylate esters was developed under mild conditions, providing the desired pyrrolidine β-amino acid derivatives in high yields (up to 98%) with excellent diastereo- and enantioselectivities (dr >20 : 1, ee up to >99%). Subsequent deprotection and hydrogenolysis of the corresponding cycloadducts could deliver highly functionalized and biologically important free pyrrolidine β-amino acids in a straightforward and efficient pathway.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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1-{[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}piperidine
CAS Number:
1218790-44-3
Molecular Formula:
C16H26BNO2S
2-Methyl-2-propanyl (1-cyclobutyl-3-hydroxy-2-propanyl)carbamate
CAS Number:
816429-99-9
Molecular Formula:
C12H23NO3
5-(6-Methoxy-1-benzofuran-2-yl)-2-(3-methyl-2-buten-1-yl)-1,3-benzenediol
CAS Number:
1017277-40-5
Molecular Formula:
C20H20O4
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