4.4 Article

Sc(OTf)3-catalyzed smooth tandem [3+2] cycloaddition/ring opening of donor-acceptor cyclopropane 1,1-diesters with enol silyl ethers

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 47, Pages 6659-6662

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.09.028

Keywords

Tandem; Cyclopropane; Cycloaddition; Enol silyl ether; Ring opening

Funding

  1. National Natural Science Foundation of China [20572045, 20421202]
  2. '111 Project' [B06005]
  3. National Key Project of Scientific and Technical Supporting Programs [2006BAE01A01-5]
  4. Ministry of Education of China [RFDF20070055022, RSF[2005]383]

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Catalyzed by Lewis acids, donor-acceptor cyclopropane 1,1-diesters reacted with enol silyl ethers to afford 1,6-dicarbonyl compounds in moderate to excellent yields. This supplied a mild carbon-carbon bond-forming method from the ring opening of cyclopropanes. A smooth tandem [3+2] cycloaddition/ring opening process has been clearly proved by an independent experiment. (C) 2008 Elsevier Ltd. All rights reserved.

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