2019
DOI: 10.1002/adsc.201901001
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Recent Advances in the Interrupted Nazarov Reaction

Abstract: In recent decades there have been significant improvements in the efficiency of synthesis as a result of considerable progress in tandem reactions, cascade transformations and related one‐pot processes. These methodologies are less time‐consuming, more cost‐effective, and produce less waste compared to the classical stepwise protocols. The Nazarov cyclization is an important and versatile method for the synthesis of five‐membered carbocycles which are found in many natural compounds and functional molecules. C… Show more

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Cited by 56 publications
(20 citation statements)
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“…Additionally, the nucleophilic interruption by a carbon nucleophile (alkenes, enols/enolates, enamines, arenes, etc.) at C2 or C4 of cation 142 also enables the formation of a QSC at either of these two carbons, as can be seen in products 144 [80–84] …”
Section: Cyclization Strategiesmentioning
confidence: 92%
“…Additionally, the nucleophilic interruption by a carbon nucleophile (alkenes, enols/enolates, enamines, arenes, etc.) at C2 or C4 of cation 142 also enables the formation of a QSC at either of these two carbons, as can be seen in products 144 [80–84] …”
Section: Cyclization Strategiesmentioning
confidence: 92%
“…The classical interrupted Nazarov reaction involves the electrocyclization of divinyl ketone providing the cyclopentenyl (oxyallyl) cation, later the addition of nucleophile afford the substituted cyclopentanones. The first step is the formation of the cyclopentenyl cation with the nucleophile, forming a mono‐addition product [70] . The scope of the interrupted Nazarov cyclisation with various substituted indoles afforded [5.8] fused‐ring systems in moderate to good yields.…”
Section: Transition‐metal Based Lewis Acid Catalyzed Transannular Cyclisation Reactionsmentioning
confidence: 99%
“…The first step is the formation of the cyclopentenyl cation with the nucleophile, forming a mono-addition product. [70] The scope of the interrupted Nazarov cyclisation with various substituted indoles afforded [5.8] fused-ring systems in moderate to good yields. The mechanism of formation of isodaucane was initiated by the coordination of Lewis acid to the unactivated double bond and formation of a.…”
Section: Transition-metal Based Lewis Acid Catalyzed Transannular Cyclisation Reactionsmentioning
confidence: 99%
“…The Nazarov cyclization reaction represents one of the most effective methods for the construction of five-membered carbocyclic rings, and it has been applied in the total synthesis of many useful natural products. Due to high stereoselectivity, high yields, and readily available starting compounds, this reaction is widely used in organic synthesis for the preparation of diverse biologically active substances [ 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 ]. However, to the best of our knowledge, this reaction was not applied for the annulation of an additional cyclopentanone ring onto the steroid skeleton.…”
Section: Introductionmentioning
confidence: 99%