N-Heterocyclic Carbene Catalyzed Reaction of Enals and 1,2-Dicarbonyl Compounds: Stereoselective Synthesis of Spiro γ-Butyrolactones
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- 4 January 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (3) , 507-509
- https://doi.org/10.1021/ol052926n
Abstract
Nucleophilic heterocyclic carbene (NHC) catalyzed annulation of enals and cyclic 1,2-dicarbonyl compounds, opening a route to γ-spirolactones, has been observed for the first time. The strategy works well with isatins, leading to spiroannulated oxindole derivatives. It is conceivable that the spiroannulation protocol reported herein will be applicable to the synthesis of important natural products that are endowed with a spiro γ-butyrolactone motif, especially oxindoles and norsesquiterpenoids.Keywords
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