4.5 Article

Diastereoselective Synthesis of Arylidene Bis(3-arylaminoacrylates) via One-pot Domino Reactions

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 31, Issue 4, Pages 479-484

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201300094

Keywords

domino reaction; electron-deficient alkyne; acrylate; isatin; stereoselectivity

Funding

  1. National Natural Science Foundation of China [21172189]
  2. Priority Academic Program Development of Jiangsu Higher Education Institutions

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The functionalized arylidene bis(3-arylaminoacrylates) were efficiently prepared by FeCl3 catalyzed one-pot domino reactions of primary amines, methyl propiolate and aromatic aldehydes. When isatins were utilized under similar conditions, only 2-oxoindolinyl 3-arylaminoacrylates were obtained in moderate yields. 1H NMR data and single crystal structures indicated that this reaction has high diastereoselectivity.

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