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Synfacts 2006(9): 0950-0950  
DOI: 10.1055/s-2006-949226
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

N-Heterocyclic Carbene Catalyzed Synthesis of 1,3,4-Trisubstituted Cyclopentenes

Contributor(s): Benjamin List, Subhas Chandra Pan
V. Nair*, S. Vellalath, M. Poonoth, E. Suresh
Regional Research Laboratory and Central Salt and Marine Chemicals Research Institute, Bhavnagar, India
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Here the authors report N-heterocyclic carbene catalyzed reaction of chalcones and enals leading to an efficient synthesis of 1,3,4-trisubstituted cyclopentenes. The catalyst 1 in combination with DBU has been found to be effective for the reaction. With 6 mol% of the catalyst, moderate to good yields (55-88%) are obtained for a variety of enals with different β-substituted chalcones. In addition, the authors have shown a plausible mechanism for the formation of the products.