One-Pot, Three-Component Synthesis of 4-Aryl-5,6-dihydropyran via Prins-Friedel-Crafts Reaction

Reddy, U. C.; Saikia, Anil K.

doi:10.1055/s-0029-1219779

Cited by 10 publications

(1 citation statement)

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“…Saikia and Reddy reported a Friedel-Crafts-terminated alkynyl Prins cyclization of aldehydes 37a and epoxides 37b with but-3-yn-1-ol (36) using BF 3 •OEt 2 in aromatic solvents (Scheme 8). 23…”

Section: Arene As Terminal Nucleophile (Intermolecular)mentioning

confidence: 99%

Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications

Abdul-Rashed¹,

Holt²,

Frontier³

2020

Synthesis

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This review focuses on alkynyl Prins and alkynyl aza-Prins cyclization processes, which involve intramolecular coupling of an alkyne with either an oxocarbenium or iminium electrophile. The oxocarbenium or iminium species can be generated through condensation- or elimination-type processes, to achieve an overall bimolecular annulation that enables the synthesis of both oxygen- and nitrogen-containing saturated heterocycles with different ring sizes and substitution patterns. Also discussed are cascade processes in which alkynyl Prins heterocyclic adducts react to trigger subsequent pericyclic reactions, including [4+2] cycloadditions and Nazarov electrocyclizations, to rapidly construct complex small molecules. Finally, examples of the use of alkynyl Prins and alkynyl aza-Prins reactions in the synthesis of natural products are described. The review covers the literature through the end of 2019.1 Introduction1.1 Alkyne-Carbonyl Coupling Pathways1.2 Coupling/Cyclization Cascades Using the Alkynyl Prins Reaction2 Alkynyl Prins Annulation (Oxocarbenium Electrophiles)2.1 Early Work2.2 Halide as Terminal Nucleophile2.3 Oxygen as Terminal Nucleophile2.4 Arene as Terminal Nucleophile (Intermolecular)2.5 Arene Terminal Nucleophile (Intramolecular)2.6 Cyclizations Terminated by Elimination3 Synthetic Utility of Alkynyl Prins Annulation3.1 Alkynyl Prins-Mediated Synthesis of Dienes for a [4+2] Cyclo- addition-Oxidation Sequence3.2 Alkynyl Prins Cyclization Adducts as Nazarov Cyclization Precursors3.3 Alkynyl Prins Cyclization in Natural Product Synthesis4 Alkynyl Aza-Prins Annulation4.1 Iminium Electrophiles4.2 Activated Iminium Electrophiles5 Alkynyl Aza-Prins Cyclizations in Natural Product Synthesis6 Summary and Outlook

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Section: Arene As Terminal Nucleophile (Intermolecular)mentioning

confidence: 99%

Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications

Abdul-Rashed¹,

Holt²,

Frontier³

2020

Synthesis

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Formation of Ethers by Alkylation of Alcohols, Phenols, and Derivatives

Larock

Kesharwani

2018

Comprehensive Organic Transformations

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Die organokatalytische asymmetrische Prins‐Cyclisierung

2015

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Wirberichten über die Entwicklung einer Brønsted-Säure-katalysierten enantioselektiven Prins-Cyclisierung.I n Anwesenheit katalytischer Mengen sterischa nspruchsvoller chiraler Imidodiphosphorsäuren reagieren Salicylaldehyde mit 3-Methyl-3-buten-1-ol zu hochfunktionalisierten 4-Methylentetrahydropyranen. Der extreme Raumbedarf der sperrigen Katalysatoren ist dabei der Schlüssel zu exzellenten Regio-und Enantioselektivität.

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One-Pot, Three-Component Synthesis of 4-Aryl-5,6-dihydropyran via Prins-Friedel-Crafts Reaction

Abstract: An efficient method for the synthesis of 4-aryldihydropyrans has been developed from the reaction of aldehydes or epoxides with homopropargylic alcohols in the presence of arenes promoted by boron trifluoride etherate

Cited by 10 publications

References 1 publication

Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications

Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications

Formation of Ethers by Alkylation of Alcohols, Phenols, and Derivatives

Die organokatalytische asymmetrische Prins‐Cyclisierung

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