Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 26, Pages 5096-5103Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100562
Keywords
Organocatalysis; Spiro compounds; Amino alcohols; Domino reactions; Michael-initiated ring-closing reaction
Categories
Funding
- Ministero Italian dell'Universita e della Ricerca (MIUR)
- University of Salerno
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An efficient cyclopropanation, by a Michael-initiated ring-closing (MIRC) reaction of 2-arylidene-1,3-indandiones and 2-arylidene malononitriles, has been developed by using different alpha-monohalogenated methylene active compounds with triethylamine. The first enantioselective cyclopropanation to spirocyclopropanes derived by the reaction of 2-arylidene-1,3-indandiones and dimethyl bromomalonate with a commercially available alpha,alpha-L-diarylprolinol as the organocatalyst and K2CO3 as the additive has been accomplished. The spirocyclopropanes were isolated in high yield and up to 85% ee. Notably, the asymmetric one-pot sequential approach to spirocyclopropanes proved to be a feasible process.
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