4.8 Article

Cooperative Photo-/Lewis Acid Catalyzed Tandem Intramolecular [3+2] Cross-Cycloadditions of Cyclopropane 1,1-Diesters with α,β-Unsaturated Carbonyls for Medium-Sized Carbocycles

Journal

ORGANIC LETTERS
Volume 17, Issue 17, Pages 4184-4187

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01928

Keywords

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Funding

  1. NSFC [21172109, 21121002]
  2. MOST (973 Project) [2010CB126106]
  3. National Key Technologies RD Program [2011BAE06B05]

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A tandem isomerization/intramolecular [3 + 2] cross-cycloaddition (IMCC) of cydopropane 1,1-diesters with alpha,beta-unsaturated ketones/aldehydes under a cooperative catalysis of photo and Lewis acids has been successfully developed. This supplied a general and efficient strategy for construction of medium-sized carbocyclic (8-, 9-, and 10-membered) skeletons as well as such carbocyde-based bridged oxa-bicyclo [n.2.1] (n = 4-6) skeletons.

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