The Catalytic, Formal Homo‐Nazarov Cyclization as a Template for Diversity‐Oriented Synthesis

Martín, Marc; Shenje, Raynold

doi:10.1002/ijch.201500099

Cited by 31 publications

(5 citation statements)

References 75 publications

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“…Successful realization of this concept will allow classification of this type of synthesis as an example of DOS. There are only a few reports on engagement of the ring opening of cyclopropane in the DOS strategy …”

Section: Introductionmentioning

confidence: 90%

Diversity-Oriented Synthesis toward Fused and Bridged Benzobicyclic Piperidin(on)es

2019

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An efficient diverse synthesis of cis-fused indenopiperidines and bridged benzomorphanones, starting from cyclopropane-fused benzomorphanothiones and benzomorphanones, respectively, using NaBH4/NiCl2·6H2O/EtOH as a reducing system, is described. High rigidity of substrates allowed axially controlled syntheses of their trans-mono-alkylated derivatives, subsequently enabling access to both trans-alkyl-functionalized benzobicyclic piperidin(on)es. Diversity-oriented synthesis of naphthalene ring-containing fused naphthoindenopiperidines and bridged naphthomorphanone directly from 2-pyridones was also performed.

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Section: Introductionmentioning

confidence: 90%

Diversity-Oriented Synthesis toward Fused and Bridged Benzobicyclic Piperidin(on)es

2019

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“…without participation of other substrate(s). Among these reactions are isomerization to acyclic or cyclic products (such as, homo‐Nazarov reaction, vinylcyclopropane‐cyclopentene rearrangement and its heteroanalogs, Cope‐like isomerization and other ring enlargement processes), a wide range of (cyclo)dimerizations as well as polymerization.…”

Section: Isomerization Of Donor‐acceptor Cyclopropanesmentioning

confidence: 99%

“…In the XXI century the focus has shifted to substrates containing two acceptor substituents (typically, two ester moieties) and (het)aryl or alkenyl group as a donor due to predominantly the ease of their synthesis . These are such compounds that were for the first time involved in several novel D‐A cyclopropane reactions such as diverse (3+n)‐cycloadditions, homo‐Nazarov cyclization, (3+n)‐annulations, wherein (het)aryl group not only serves as a donor substituent but also participates in the new ring formation, as well as various dimerizations. Moreover, D‐A cyclopropanes have been successfully introduced into dynamic kinetic asymmetric transformations (DYKAT) .…”

Section: Introductionmentioning

confidence: 99%

Donor‐Acceptor Cyclopropanes in the Synthesis of Carbocycles

Ivanova

Trushkov

2019

The Chemical Record

109

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Donor‐acceptor cyclopropanes not only participate in a broad range of ring openings with nucleophiles, electrophiles, radical and red‐ox agents, but also are excellent substrates for various (3+n)‐cycloaddition and (3+n)‐annulation processes. Moreover, under treatment with Lewis acid donor‐acceptor cyclopropanes can produce new ring systems via isomerization or cyclodimerization. Authors’ contribution to the synthesis of diverse carbocycles from donor‐acceptor cyclopropanes is summarized in this account.

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“…The first step involves the catalyzed cyclopropane ring opening giving oxohexadienyl cation 159 . The subsequent intramolecular cyclization via electrophilic substitution gives cyclohexenylallyl cation 160 , which either eliminates a proton resulting in cyclohexanone 161 or adds a nucleophile affording a mixture of isomers 162a and b .…”

Section: Interrupted Nazarov‐type Reactionmentioning

confidence: 99%

Recent Advances in the Interrupted Nazarov Reaction

Yadykov

Ширинян

2019

Adv Synth Catal

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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. Current activities in the field of the Nazarov reaction are focused on development of better catalysts, asymmetric options and increasing the efficiency of synthesis. This transformation is suitable for applying to an intensified step‐economy in interrupted versions and one‐pot protocols. Interrupted Nazarov reactions in particular take advantage of the stereospecific nature of the electrocyclization. The universality of these reactions has facilitated an access to a plethora of complex small molecules of high medicinal relevance. In this review, we present a comprehensive summary of recent advances in the interrupted Nazarov‐type cyclization, and classify these reactions according to the structure of the substrate or the reaction mechanism. This is the first review that presents a survey on various types of interrupted Nazarov cyclization and deals with the recent advances, especially using tandem/domino or one‐pot reaction strategies and covers the literature from 2009 to 2019.

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The Catalytic, Formal Homo‐Nazarov Cyclization as a Template for Diversity‐Oriented Synthesis

Cited by 31 publications

References 75 publications

Diversity-Oriented Synthesis toward Fused and Bridged Benzobicyclic Piperidin(on)es

Diversity-Oriented Synthesis toward Fused and Bridged Benzobicyclic Piperidin(on)es

Donor‐Acceptor Cyclopropanes in the Synthesis of Carbocycles

Recent Advances in the Interrupted Nazarov Reaction

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