Polycyclic Azetidines and Pyrrolidines via Palladium-Catalyzed Intramolecular Amination of Unactivated C(sp3)-H Bonds
Zhao, Jie1,2; Zhao, Xiao-Jing1,2; Cao, Pei1; Liu, Ji-Kai3; Wu, Bin1,3
2017-09-15
Source PublicationORGANIC LETTERS
ISSN1523-7060
Volume19Issue:18Pages:4880-4883
AbstractA novel strategy to construct complex poly cyclic nitrogen-containing heterocycles from aliphatic amines via picolinamide-assisted palladium-catalyzed C-H bond activation reaction was reported. The reaction exhibits broad substrate scope for the synthesis of various azabicyclic scaffolds, including azetidines and tropane-class alkaloids. Application of this method to naturally occurring (-)-cis-myrtanylamine, an unprecedented type of carbon-carbon bond activation, in which the electron-pair involved initiates an intramolecular "S(N)2-like" displacement of a cyclopalladium-fragment from a tertiary center, is described.
KeywordC-h Functionalization c(Sp(3))-h Bonds Beta-lactams Stereoselective-synthesis Organic-synthesis Aliphatic-amines Activation Derivatives Cyclization Amidation
Subject AreaChemistry, Organic
DOI10.1021/acs.orglett.7b02339
Indexed BySCI
Language英语
WOS IDWOS:000411304300045
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/54881
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming Inst Bot, Kunming 650201, Yunnan, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.South Cent Univ Nationalities, Sch Pharmaceut Sci, Wuhan 430074, Hubei, Peoples R China
Recommended Citation
GB/T 7714
Zhao, Jie,Zhao, Xiao-Jing,Cao, Pei,et al. Polycyclic Azetidines and Pyrrolidines via Palladium-Catalyzed Intramolecular Amination of Unactivated C(sp3)-H Bonds[J]. ORGANIC LETTERS,2017,19(18):4880-4883.
APA Zhao, Jie,Zhao, Xiao-Jing,Cao, Pei,Liu, Ji-Kai,&Wu, Bin.(2017).Polycyclic Azetidines and Pyrrolidines via Palladium-Catalyzed Intramolecular Amination of Unactivated C(sp3)-H Bonds.ORGANIC LETTERS,19(18),4880-4883.
MLA Zhao, Jie,et al."Polycyclic Azetidines and Pyrrolidines via Palladium-Catalyzed Intramolecular Amination of Unactivated C(sp3)-H Bonds".ORGANIC LETTERS 19.18(2017):4880-4883.
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