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Issue 3, 2017
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A [3 + 2]–[4 + 2]–[3 + 2] cycloaddition sequence of isoquinolinium ylide

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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.

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

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Supplementary files

Article information


Submitted
07 Oct 2016
Accepted
09 Dec 2016
First published
12 Dec 2016

Org. Chem. Front., 2017,4, 354-357
Article type
Research Article

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

R. Liu, R. Shi, J. Sun and C. Yan, Org. Chem. Front., 2017, 4, 354 DOI: 10.1039/C6QO00615A

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