4.7 Article

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

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 9, 页码 4774-4783

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00461

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资金

  1. NSFC-Shandong Joint Fund for Marine Science Research Centers [U1606403]
  2. Qingdao National Laboratory for Marine Science and Technology [2015ASKJ02-06]
  3. Fundamental Research Funds for the Central Universities [201562031]

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The asymmetric organocatalyzed diversity-oriented one-pot synthesis has been developed to construct chroman2-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-beta-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.

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