2017
DOI: 10.1002/ejoc.201700633
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Recent Advances in Prins Spirocyclization

Abstract: The classical Prins cyclization has been one of the most intensively studied reactions during the last two decades, and it has found many applications in key steps of natural product syntheses, especially for products containing tetrahydropyran motifs and related structures in their core skeletons. The application of this reaction to the synthesis of spirocylic networks has made substantial progress recently. Spiro motifs are found in many natural products with promising biorelevance and are increasingly being… Show more

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Cited by 45 publications
(6 citation statements)
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“…The Prins reaction is a powerful and versatile methodology for the construction of oxygenated heterocyclic compounds. This reaction, together with its N - and S -variants, has been extensively used for the preparation of different-ring-size carbo- or heterocycles in the so-called Prins cyclization, a transformation that requires the use of an aldehyde or a related compound, an alkene (the so-called π-component) and a nucleophile, in a process that is typically promoted by a Lewis or Brønsted acid (Scheme ). The key step on this reaction is the formation of an oxocarbenium ion that reacts with 1 equiv of the π-component in an intermolecular (Scheme , top) or intramolecular fashion (Scheme , bottom).…”
Section: Introductionmentioning
confidence: 99%
“…The Prins reaction is a powerful and versatile methodology for the construction of oxygenated heterocyclic compounds. This reaction, together with its N - and S -variants, has been extensively used for the preparation of different-ring-size carbo- or heterocycles in the so-called Prins cyclization, a transformation that requires the use of an aldehyde or a related compound, an alkene (the so-called π-component) and a nucleophile, in a process that is typically promoted by a Lewis or Brønsted acid (Scheme ). The key step on this reaction is the formation of an oxocarbenium ion that reacts with 1 equiv of the π-component in an intermolecular (Scheme , top) or intramolecular fashion (Scheme , bottom).…”
Section: Introductionmentioning
confidence: 99%
“…[3][4][5][6][7][8] Common methodologies for assembling spirocyclic scaffolds are mainly relaying on intramolecular S N 2 alkylation [9][10][11][12][13][14][15][16][17][18][19] and Nacylation, [11,20,21] ring closing metathesis [20,[22][23][24] of the appropriate precursors. Additionally, metal-catalyzed [25][26][27][28] and hypervalent iodine mediated [29] dearmoatization reactions, Prins reaction [30][31][32] and cycloaddition reactions [23,[33][34][35] should be mentioned.…”
Section: Introductionmentioning
confidence: 99%
“…1a). Beyond the conventional methods for the synthesis of bio-relevant spirocycles, 1,9,10 recently, several enthralling methods have been disclosed relying on advances in transition metal [11][12][13] and photoredox catalysis. 14 The oxidative dearomatisation of phenols and their derivatives is a powerful tool for assembling spirocycles; [15][16][17] however, commonly used methods for cyclisations require the use of hypervalent iodine reagents, 18 (over) stoichiometric amounts of transition metal salts 19,20 or peroxo compounds 21 as oxidants.…”
mentioning
confidence: 99%