4.5 Article

Highly Enantioselective Direct Michael Addition of 1H-Benzotriazole to Chalcones Catalyzed by Sc(OTf)3/N,N′-Dioxide Complex

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 11, Pages 2039-2042

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100021

Keywords

Asymmetric synthesis; Michael addition; Nitrogen heterocycles; Chalcones

Funding

  1. National Natural Science Foundation of China [20732003, 21021001]
  2. National Basic Research Program of China (973 Program) [2011CB808600]

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The N,N'-dioxide-Sc(OTf)(3) complex was applied in the asymmetric Michael reaction of 1H-benzotriazole with chalcones to give the corresponding N-1 products in excellent yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Further transformation into other optically active derivatives such as beta-benzotriazolyl ester, alcohol, and amide were also realized with excellent results.

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