Recent advances in the direct transformation of propargylic alcohols to allenes

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(23), С. 6760 - 6782

Опубликована: Янв. 1, 2021

This review summaries a view of the advances in direct transformation propargylic alcohols to functionalized allenes.

Язык: Английский

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Chiral phosphoric acid-catalyzed regio- and enantioselective reactions of functionalized propargylic alcohols

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(5), С. 1234 - 1240

Опубликована: Янв. 1, 2022

Chiral phosphoric acid has been utilized for covalent activation of propargylic alcohols to act as pre-catalyst. With this mode, a range highly regio- and enantioenriched heterocyclic products could be generated efficiently from racemic alcohols.

Язык: Английский

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Organocatalytic Enantioselective 1,10-Addition of Alkynyl Indole Imine Methides with Thiazolones: An Access to Axially Chiral Tetrasubstituted Allenes

Organic Letters, Год журнала: 2022, Номер 24(27), С. 4914 - 4918

Опубликована: Июнь 30, 2022

An asymmetric organocatalytic remote 1,10-addition of alkynyl indole imine methides generated in situ from α-(6-indolyl) propargylic alcohols with thiazolones has been developed for the first time, affording axially chiral tetrasubstituted allenes featuring vicinal sulfur-containing quaternary carbon stereocenters high yields excellent stereoselectivities. The representative scale-up reaction and transformations 1,10-adduct were examined. mechanism was expounded by control experiments DFT calculations.

Язык: Английский

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Catalyst-Controlled Divergent Reactions of 2,3-Disubstituted Indoles with Propargylic Alcohols: Synthesis of 3H-Benzo[b]azepines and Axially Chiral Tetrasubstituted Allenes

Organic Letters, Год журнала: 2022, Номер 24(35), С. 6472 - 6476

Опубликована: Авг. 30, 2022

Catalyst-controlled divergent reactions of 2,3-disubstituted indoles with propargylic alcohols were developed for the first time. In presence TsOH or B(C6F5)3 as catalyst, reacted smoothly 3-alkynyl-3-hydroxyisoindolinones to afford 3H-benzo[b]azepines by selective C2(sp2)-C3(sp2) ring expansion indoles. contrast, decreasing catalyst strength (e.g., chiral phosphoric acid) interrupted cascade reactions, affording axially tetrasubstituted allenes bearing an adjacent quaternary carbon stereocenter. Control experiments provided insights into reaction mechanism.

Язык: Английский

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Organocatalytic enantioselective reaction of tertiary α-(7-indolyl)methanols with tryptamines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(14), С. 3662 - 3668

Опубликована: Янв. 1, 2023

With the aid of chiral phosphoric acid, enantioselective 1,6-addition tryptamines to in situ formed alkynyl 7-methylene-7 H -indoles from tertiary α-(7-indolyl)methanols has been established, furnishing axially tetrasubstituted allenes high yields.

Язык: Английский

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Recent Progress in Application of Propargylic Alcohols in Organic Syntheses

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(18), С. 2991 - 3019

Опубликована: Июль 14, 2023

Abstract Propargylic alcohols are readily available bifunctional (alkyne and hydroxyl groups) synthons, which recognize as one of the attractive synthetic feedstock in organic transformations. Especially, recent years employment these valuable molecules has frequently been observed literature. Hence, present review highlights advancements application propargylic cyclization, substitution, addition reactions.

Язык: Английский

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Transition Metal‐Catalyzed Hydroalkoxylation of Alkynes: An Overview

Chemistry - A European Journal, Год журнала: 2021, Номер 27(63), С. 15571 - 15604

Опубликована: Авг. 3, 2021

Oxygen-bearing motifs, mainly the congener heterocycles are ubiquitous due to their presence in various natural products and bioactive scaffolds. Although literature, several strategies have been developed for synthesis, hydroalkoxylation of alkynes has come forward as a method choice used extensively. In particular, gained enormous attention from synthetic community rapid access very useful reactive intermediate like 'enol ether'. Furthermore, manifold utility these methods, reports elaborating generation ether' using usage reactions cascade or tandem manner. This review focuses on recent development synthesis oxygen-containing entities.

Язык: Английский

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Recent advances in the cascade reactions of enynols/diynols for the synthesis of carbo- and heterocycles

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(20), С. 5643 - 5674

Опубликована: Янв. 1, 2022

This review summaries a view of the advances in cascade reactions enynols/diynols for construction carbo- and heterocycles.

Язык: Английский

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Recent approaches for the synthesis of pyridines and (iso)quinolines using propargylic Alcohols

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(31), С. 6037 - 6056

Опубликована: Янв. 1, 2022

This review article contains various synthetic strategies for the generation of pyridines, quinolines, and isoquinolines from propargylic alcohols during period between 2005–2021. is first focused that has appeared on this topic.

Язык: Английский

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Direct Synthesis of Benzo[b]fluorenyl Thiophosphates via Tandem Cyclization of Diynols with (RO)₂P(O)SH

Organic Letters, Год журнала: 2023, Номер 25(8), С. 1263 - 1267

Опубликована: Фев. 16, 2023

A general and metal-free protocol for the construction of benzo[b]fluorenyl thiophosphates was developed through cascade cyclization easily prepared diynols (RO)2P(O)SH, with water as only byproduct. The novel transformation involved allenyl thiophosphate key intermediate, followed by Schmittel-type to achieve desired products. Notably, (RO)2P(O)SH acted not a nucleophile but also an acid-promoter initiate reaction.

Язык: Английский

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