A [3 + 2]–[4 + 2]–[3 + 2] cycloaddition sequence of isoquinolinium ylide

文献情報

出版日 2016-12-12

DOI 10.1039/C6QO00615A

インパクトファクター 5.281

著者

Ruzhang Liu, Rong-Guo Shi, Jing Sun, Chao-Guo Yan

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 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

A [3 + 2]–[4 + 2]–[3 + 2] cycloaddition sequence of isoquinolinium ylide

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