N-Heterocyclic carbene catalyzed reaction of enals and 1,2-dicarbonyl compounds: stereoselective synthesis of spiro γ-butyrolactones

Nair, Vijay ; Vellalath, Sreekumar ; Poonoth, Manojkumar ; Mohan, Resmi ; Suresh, Eringathodi (2006) N-Heterocyclic carbene catalyzed reaction of enals and 1,2-dicarbonyl compounds: stereoselective synthesis of spiro γ-butyrolactones Organic Letters, 8 (3). pp. 507-509. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol052926n

Related URL: http://dx.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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:84093
Deposited On:24 Feb 2012 06:15
Last Modified:24 Feb 2012 06:15

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