Recent Advances in Stetter Reaction and Related Chemistry: An update
The Stetter reaction is actually a special C−C bond forming reaction through a 1,4‐addition reaction in the presence of nucleophilic catalyst. It involves a reaction between aldehydes and Michael acceptors catalyzed by N‐heterocyclic carbenes (NHC's) leading to preparation of 1,4‐dicarbonyl com...
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Veröffentlicht in: | Asian journal of organic chemistry 2020-12, Vol.9 (12), p.1999-2034 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | The Stetter reaction is actually a special C−C bond forming reaction through a 1,4‐addition reaction in the presence of nucleophilic catalyst. It involves a reaction between aldehydes and Michael acceptors catalyzed by N‐heterocyclic carbenes (NHC's) leading to preparation of 1,4‐dicarbonyl compounds via carbon‐carbon bond formation. It offers a powerful approach to access 1,4‐dicarbonyl compounds which are significant starting materials and intermediates in the synthesis of several heterocyclic systems, and bioactive heterocyclic framework which are present in natural products. In this review we try to underscore the recent advances in Stetter reaction and its applications from 2015 till date. Notably, we focused on the applications of Stetter reaction in the synthesis of various heterocyclic systems and total synthesis of natural products, which have largely been overlooked, previously.
The Stetter reaction is the 1,4‐conjugate addition of an aldehyde to an a,β‐unsaturated compound, initially catalyzed by cyanide, and developed being catalyzed by a thiazolium salt or NHCs. In this review, we tried to describe different kinds of Stetter inducing inter and intramolecular, dual Stetter reaction, Stetter cascade and radically Stetter reaction. Particularly, we tried to disclose how the Stetter reaction is important, playing a vital role in the crucial step of the total synthesis of natural products and biologically actives compounds, which are completed in multistep fashio. |
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ISSN: | 2193-5807 2193-5815 |
DOI: | 10.1002/ajoc.202000378 |