Transposition of an acrylate moiety in TMSOTf-mediated reaction of alkynyl vinylogous carbonates gives heterocyclic dienes

Gharpure, Santosh J.; Fartade, Dipak J.; Gupta, Krishna S.; Patel, Raj K.

doi:10.1039/d2cc03802a

Cited by 6 publications

(1 citation statement)

References 45 publications

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“…The method involved TMSOTf mediated reaction of alkynyl vinylogous carbonates 99 to give 1,4‐oxazepine and dihydropyran embedded dienes 100 – 101 (Scheme 33). [74] The formation of diene can be explained via the transposition of ethyl acrylate moiety involving intramolecular cascade Prins type cyclization/retro‐ oxa ‐Michael reaction/cycloisomerization ( Int ‐ BE ‐ BF ). The reaction was found to have a broad substrate scope, and alkynes with electron donating as well as withdrawing group substituted aryl alkynes were found to react smoothly to furnish the corresponding dihydropyrans 101 in good to excellent yield and diastereoselectivity.…”

Section: Carboalkoxylationmentioning

confidence: 99%

New Avenues for the Synthesis of Oxa‐Cycles Using Lewis/Brønsted Acid Mediated Carboxygenation and Carboalkoxylation of Alkynes

Nanda,

Pal

et al. 2024

Eur J Org Chem

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The cascade functionalizations of alkynes have provided many elegant methods for the synthesis of useful scaffolds. Amongst these functionalizations, the ones comprising C‐C and C‐O bond formation have been utilized extensively due to the abundant presence of oxygenated motifs in various bio‐active natural as well as unnatural products. Transition‐metal catalysis is a mainstay for these tandem functionalizations as they are very efficient. However, their utilization does typically involve stoichiometric additives like other metal salts and/or Lewis acids/Brønsted acids (LA/BA). Thus, approaches that rely solely on using LA/BA, make these vital transformations not only eco‐friendly and atom economical but also cost beneficial are fast emerging as complementary alternatives. The present review addresses the gap in the literature by summarizing recent developments in LA/BA mediated 1,1/1,2‐carboxygenation and carboalkoxylation of alkynes for the synthesis of oxa‐cycles. The reaction mechanisms are particularly emphasized to bring out understanding needed from the point of future developments in this domain.

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Section: Carboalkoxylationmentioning

confidence: 99%

New Avenues for the Synthesis of Oxa‐Cycles Using Lewis/Brønsted Acid Mediated Carboxygenation and Carboalkoxylation of Alkynes

Nanda,

Pal

et al. 2024

Eur J Org Chem

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Synthesis of Sulfonyl Arenes via Hydroxy/Amino‐Benzannulation of Sulfonyl Enynals

Gharpure,

Somani,

Fartade

2023

Adv Synth Catal

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An Acid Catalyzed Alkynyl‐Prins Cyclization‐Rearrangement Cascade of 2‐(Alkynol)Benzoates: An Approach to 3‐Alkyl‐[n,5]‐Oxaspirophthalides

Mishra,

Baire

2024

Adv Synth Catal

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The oxaspiro‐phthalides ([n,5]‐oxaspirobenzalactones) bearing a phthalide spirofused to a cyclic‐ether of various sizes are frameworks found in bioactive natural products. The discovery and development of an alkynyl‐Prins cyclization based, strategy for the construction of structurally interesting, medicinally useful [5,5]‐ [6,5]‐, and [7,5]‐oxaspirophthalides is reported in this manuscript. Our strategy may represent the first report on the construction of oxaspiro‐phthalides using the alkynyl‐Prins cyclization. This approach exhibits broad substrate scope with respect to carbonyl compounds and 2‐(alkynol)benzoates, with yields ranging between 71‐98%. Isolation of intermediate, and further conversion of it to the end‐product supported the proposed mechanistic pathway.

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Transposition of an acrylate moiety in TMSOTf-mediated reaction of alkynyl vinylogous carbonates gives heterocyclic dienes

Cited by 6 publications

References 45 publications

New Avenues for the Synthesis of Oxa‐Cycles Using Lewis/Brønsted Acid Mediated Carboxygenation and Carboalkoxylation of Alkynes

New Avenues for the Synthesis of Oxa‐Cycles Using Lewis/Brønsted Acid Mediated Carboxygenation and Carboalkoxylation of Alkynes

Synthesis of Sulfonyl Arenes via Hydroxy/Amino‐Benzannulation of Sulfonyl Enynals

An Acid Catalyzed Alkynyl‐Prins Cyclization‐Rearrangement Cascade of 2‐(Alkynol)Benzoates: An Approach to 3‐Alkyl‐[n,5]‐Oxaspirophthalides

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