Recent developments in one-pot stepwise synthesis (OPSS) of small molecules

iScience, Год журнала: 2022, Номер 25(9), С. 105005 - 105005

Опубликована: Авг. 28, 2022

One-pot synthesis is an active topic in organic chemistry due to its intrinsic advantages of simple operation, high mass efficiency, low cost, and less amount waste disposal. Among three kinds one-pot syntheses, 1) cascade reactions, 2) multicomponent reactions (MCRs), 3) stepwise (OPSS), OPSS could be more flexible practical since it carried out stepwisely have variable reaction conditions for different steps. This perspective article uses selected examples highlight the recent development involving cyclization, cycloaddition, rearrangement, catalytic heterocyclic scaffolds, asymmetric molecules, natural products, bioactive compounds.

Язык: Английский

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Diastereo‐ and Enantioselective Synthesis of Bisbenzannulated Spiroketals and Spiroaminals by Ir/Ag/Acid Ternary Catalysis

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(42)

Опубликована: Авг. 4, 2022

Abstract We reported herein an iridium/silver/acid ternary catalytic system to access bisbenzannulated [6,6]‐spiroketals in high efficiency with generally diastereo‐ and enantioselectivities (up >20 : 1 dr, >99 % ee). In this procedure, readily available o ‐alkynylacetophenones undergo cycloisomerization generate isochromenes situ that participate stereoselective allylation/spiroketalization sequence 2‐(1‐hydroxyallyl)phenols. Meanwhile, 2‐(1‐hydroxyallyl)anilines were also compatible cascade reaction, furnishing structurally novel [6,6]‐spiroaminals good diastereoselectivities (8 1–12 dr) excellent (98 %–>99 Moreover, experimental studies theoretical calculations performed illustrate the reaction mechanism stereochemistry.

Язык: Английский

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Stereoretentive Catalytic [3+2]-Cycloaddition/Rearrangement/Decarboxylation Reactions of Indoles with Non-Racemic Donor–Acceptor Cyclopropanes

ACS Catalysis, Год журнала: 2023, Номер 13(3), С. 1621 - 1629

Опубликована: Янв. 12, 2023

A highly enantioselective synthesis of chiral dihydro-3H-carbazole-2-carboxylate derivatives is reported via a "one-pot" cyclopentannulation-rearrangement cascade reaction that sequentially catalyzed by nickel(II) perchlorate hexahydrate and scandium(III) trifluoromethanesulfonate with 3-methylindole non-racemic donor–acceptor cyclopropanes in high yields enantioretention under mild conditions. Highly diastereoselective [3+2]-cycloaddition dependent on substituents. In addition, further transformation these dihydro-3H-carbazole-2-carboxylates hydrolysis decarboxylation unexpectedly conditions provides straightforward access to the decarboxylated compounds moderate retention enantiomeric purity.

Язык: Английский

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Ir-Catalyzed Asymmetric Cascade Allylation/Spiroketalization Reaction for Stereoselective Synthesis of Oxazoline-Spiroketals

Organic Letters, Год журнала: 2023, Номер 25(2), С. 325 - 330

Опубликована: Янв. 6, 2023

An asymmetric cascade allylation/spiroketalization reaction between 2-(1-hydroxyallyl)phenols and 5-methyleneoxazolines is accomplished by using a chiral Ir(I) catalyst derived from commercially available iridium precursor the Carreira ligand. This protocol furnishes class of structurally novel unique oxazoline-spiroketals in up to 86% yield, >99% ee >20:1 dr. Moreover, control experiments reveal that 4,4-disubstitution on necessary avoid aromatization for spiroketalization occur. On basis this, plausible mechanism illustrated.

Язык: Английский

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Stereoretentive Catalytic [3 + 2]/[3 + 3]-Cycloaddition of Nonracemic Donor–Acceptor Cyclopropanes: Synthesis of Substituted Pyrrolidines and 1,2-Oxazinanes

Organic Letters, Год журнала: 2023, Номер 25(17), С. 3029 - 3033

Опубликована: Апрель 20, 2023

A highly enantioselective preparation of substituted pyrrolidines and 1,2-oxazinanes has been achieved via stereoretentive [3 + 2]/[3 3]-cycloaddition nonracemic donor-acceptor cyclopropanes with imines, triazines, nitrones in good to high yields broad scope under mild reaction conditions. In comparison the well-documented approach cyclopropane reactions using racemic reactants a catalyst chiral ligands, this report features applications enantioenriched as cycloadduct achiral catalysts.

Язык: Английский

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Mechanistic insights and stereoselectivity in Ni(II)-catalyzed asymmetric [3 + 2]/[3 + 3] cycloaddition reactions of donor-acceptor cyclopropanes: A DFT study

Molecular Catalysis, Год журнала: 2025, Номер 579, С. 115034 - 115034

Опубликована: Март 24, 2025

Язык: Английский

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Recent advances in asymmetric synthesis via cyclopropanol intermediates

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 4, 2024

The review summarizes achievements in stereoselective and stereoretentive transformations of cyclopropanols suitable for asymmetric synthesis.

Язык: Английский

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Advances in the Catalytic Asymmetric Synthesis of Chiral Spiroketals

Chinese Journal of Organic Chemistry, Год журнала: 2022, Номер 42(11), С. 3640 - 3640

Опубликована: Янв. 1, 2022

As an unique spiro skeleton, spiroketals are ubiquitous motifs in many natural products, biologically active molecules, and privileged chiral ligands.The development of efficient synthetic methods for the preparation has long been a hot research topic organic synthesis.In particular, remarkable advances regarding catalytic asymmetric synthesis have achieved over past decade.The progress field is summarized according to reaction types.The future direction this also prospected.

Язык: Английский

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(Z)-5-Benzylidene-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole

Molbank, Год журнала: 2023, Номер 2023(1), С. M1600 - M1600

Опубликована: Март 6, 2023

By strategic use of the valence difference between hard gold(III) and soft gold(I) catalysts, one-pot synthesis (Z)-5-benzylidene-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole (15) from propargylic alcohol (9) p-toluamide (13) was achieved via gold(III)-catalyzed substitution followed by gold(I)-catalyzed cyclization. The structure 15 confirmed X-ray crystallographic analysis.

Язык: Английский

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(E)-5-[Bromo(phenyl)methylene]-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole

Molbank, Год журнала: 2024, Номер 2024(1), С. M1769 - M1769

Опубликована: Фев. 2, 2024

One-pot synthesis of (E)-5-[bromo(phenyl)methylene]-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole (9) from propargylic alcohol 5 and p-toluamide (6) was achieved via gold(III)-catalyzed substitution, followed by bromocyclization. The structure 9 confirmed an X-ray crystallographic analysis.

Язык: Английский

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