Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes

Shenje, Raynold; Williams, Corey W.; Francois, Katherine M.

doi:10.1021/ol503305r

Cited by 28 publications

(7 citation statements)

References 49 publications

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“…Chemodivergent syntheses are of great value for obtaining skeletal divergence in organic and medicinal chemistry . Over the past few decades, chemoselective control achieved utilizing metal catalysts and solvents has received increasing attention, while relatively few papers have described temperature‐dependent reactions . However, since being first discovered by Woodward and Baer in 1944, kinetic and thermodynamic control of reactions have remained as important topics in organic synthesis for enhancing reaction efficiency and for increasing molecular diversity.…”

Section: Methodsmentioning

confidence: 99%

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Zhou

Jia

et al. 2017

Asian J Org Chem

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Section: Methodsmentioning

confidence: 99%

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Zhou

Jia

et al. 2017

Asian J Org Chem

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“…A method involving the interrupted homo ‐Nazarov cyclization of donor–acceptor cyclopropyl vinyl ketones 166 with allylsilane as external nucleophile has been developed (Scheme ) . The pathway of this cascade reaction was found to be highly dependent on the amount of Lewis acid.…”

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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“…Towards addressing these limitations, we developed a Lewis acid‐catalyzed protocol for the allylsilane‐interrupted homo‐Nazarov cyclization (Scheme ) . By employing D‐A‐A cyclopropanes 44 and allylsilanes 45 , 6‐allyl cyclohex‐1‐en‐1‐ols 46 were generated following a Hosomi‐Sakurai allylation of the cyclic oxylallyl cation intermediate.…”

Section: Reagent‐based Dos Approachesmentioning

confidence: 99%

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

Martín

Shenje

2016

Israel Journal of Chemistry

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Since the formal characterization of diversity‐oriented synthesis (DOS), identification of effective examples of DOS remains an important endeavor for synthetic and pharmaceutical chemists requiring new strategies to generate broader skeletal diversity. Over the last decade, the formal homo‐Nazarov cyclization has been an increasingly popular strategy for the concise assembly of functionalized six‐membered rings due to the advent of catalytic methods to promote the transformation under milder reaction conditions. Moreover, using the formal homo‐Nazarov cyclization as a mechanistic template, reactions can be strategically devised as an effort towards diversity‐oriented synthesis. The resulting “homo‐Nazarov‐inspired” reactions are then demonstrated as a means to access broad structural diversity. This review discusses the development of these catalytic approaches and the successful implementation of the formal homo‐Nazarov reaction as a viable template for diversity‐oriented synthesis.

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Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes

Cited by 28 publications

References 49 publications

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Temperature‐Controlled Base‐Promoted Cyclization for the Synthesis of 2‐Amino‐4H‐benzo[d][1,3]thiazin‐4‐ones and 2‐Thioxo‐4(3H)‐quinazolinones

Recent Advances in the Interrupted Nazarov Reaction

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

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