A [3 + 2]–[4 + 2]–[3 + 2] cycloaddition sequence of isoquinolinium ylide
Literature Information
Publication Date
2016-12-12
DOI
10.1039/C6QO00615A
Impact Factor
5.281
Authors
Ruzhang Liu, Rong-Guo Shi, Jing Sun, Chao-Guo Yan
View Original
Abstract
A unique [3 + 2]–[4 + 2]–[3 + 2] cycloaddition sequence of isoquinolinium ylide with aromatic aldehydes and indan-1,3-dione is investigated to afford polycyclic compounds with ten stereogenic centers in moderate to high yields. In this three-component reaction, the isoquinolinium salt has a triple function as a 1,3-dipole, an electron-rich dienophile and an electron-deficient diene. The observance of only one diastereomer verified the very high regio- and diastereo-selectivity, and the mechanistic rationale for the stereoselectivity is also discussed.
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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
(S)-3-((tert-Butoxycarbonyl)amino)-4-(4-(tert-butyl)phenyl)butanoic acid
CAS Number:
403661-85-8
Molecular Formula:
C19H29NO4
![6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine structure](https://static.chemtradehub.com/structs/103/1033202-59-3-2a8f.webp "6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine structure")
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