Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Diversity-Oriented One-Pot Synthesis to Construct Functionalized Chroman-2-one Derivatives and Other Heterocyclic Compounds

Diversity-Oriented One-Pot Synthesis to Construct Functionalized Chroman-2-one Derivatives and Other Heterocyclic Compounds
Hua-Shi Guan, Ying-Han Chen, Yan-Kai Liu, Xue-Li Sun
The asymmetric organocatalyzed diversity-oriented one-pot synthesis has been developed to construct chroman-2-one derivatives and other heterocyclic compounds with excellent efficiency and stereoselectivity. The reactions represent a challenging issue, since it altered the inherent selectivity profiles exhibited by the substrates of 2-hydroxycinnamaldehyde 1 and trans-β-nitrostyrene 2, which was previously reported as the asymmetric oxa-Michael–Michael cascade to generate chiral chromans. It should be noted that polycyclic O,O-acetal-containing compounds, which are found in numerous natural products and biologically interesting molecules, could also be achieved in good yields with excellent enantioselectivity as a single diastereoisomer with five continuous stereogenic centers.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00461

DOI: 10.1021/acs.joc.7b00461

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