4.7 Article

Organocatalytic Enantioselective Tandem Michael Addition and Cyclization Reaction of Trisubstituted 2-Nitro-1,3-enynes with Cyclic 1,3-Diketones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 11, Pages 1892-1900

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700085

Keywords

chromenes; cyclization; enynes; Michael addition; organocatalysis

Funding

  1. National Natural Science Foundation of China [21572086, 21572085, 201272098]
  2. 111 Project

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An enantioselective tandem Michael addition/ cyclization reaction between trisubstituted 2-nitro-1,3-enynes and cyclic 1,3-diketones catalyzed by a chiral organosquaramide catalyst in the presence of Ag2CO3 was developed. The chiral functionalized chromene products could be obtained in good yield and in 80-99% enantiomeric excess. The structures and absolute configurations of some of the products were confirmed by X-ray crystallographic analysis.

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