Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 4, Issue 3, Pages 354-357Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6qo00615a
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- National Natural Science Foundation of China [21572196]
- Priority Academic Program Development of Jiangsu Higher Education Institutions [BK2013016]
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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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