Highly efficient construction of 2,3-disubstituted indoline derivatives by [4 + 1] annulation of sulfur ylides and o-sulfonamido aldimines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(6), С. 1521 - 1526

Опубликована: Янв. 1, 2023

A highly efficient [4 + 1] annulation of sulfur ylide salts and o -sulfonamido aldimines for construction valuable 2,3-disubstituted indolines is reported. It worth noting that indoles could also be synthesized by this cascade reaction.

Язык: Английский

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Asymmetric Synthesis of Spiro[Azetidine‐3,3′‐Indoline]‐2,2′‐Diones via Copper(I)‐Catalyzed Kinugasa/C−C Coupling Cascade Reaction

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

Опубликована: Сен. 2, 2022

Abstract Spiro[azetidine‐indolines] are important scaffolds in diverse bioactive compounds. Current efforts to synthesize spiro[azetidine‐indolines] limited chiral spiro[azetidine‐2,3′‐indolines]. Asymmetric synthesis of structurally similar spiro[azetidine‐3,3′‐indolines] remains unexplored. In this work, the first copper(I)‐catalyzed asymmetric Kinugasa/aryl C−C coupling cascade reaction is described. This provides a straightforward access densely functionalized spiro[azetidine‐3,3′‐indoline]‐2,2′‐diones good yields and with high enantioselectivity.

Язык: Английский

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Enantioselective Synthesis of Azetidines through [3 + 1]-Cycloaddition of Donor–Acceptor Aziridines with Isocyanides

Organic Letters, Год журнала: 2022, Номер 24(7), С. 1513 - 1517

Опубликована: Фев. 11, 2022

The enantioselective [3 + 1]-cycloaddition of racemic donor-acceptor (D-A) aziridines with isocyanides was first realized under mild reaction conditions using a chiral N,N'-dioxide/MgII complex as catalyst, providing facile route to enantioenriched exo-imido azetidines good excellent yield (up 99%) and enantioselectivity 94% ee). An obvious amplification effect observed in this system, an explanation elucidated based on the experimental investigation X-ray crystal structure enantiomerically pure catalyst.

Язык: Английский

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α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

ChemistryOpen, Год журнала: 2024, Номер unknown

Опубликована: Июль 11, 2024

Abstract This review introduces the synthetic organic chemical value of α‐bromocarbonyl compounds with tertiary carbons. compound a carbon has been used primarily only as radical initiator in atom transfer polymerization (ATRP) reactions. However, recent development photo‐radical reactions (around 2010), research on use alkyl precursors became popular 2012). As more examples were reported, studied not radicals but also for their applications organometallic and ionic That is, act nucleophiles well electrophiles. The carbonyl group is attractive because it allows skeleton to be converted after reaction, being applied total synthesis. In our survey until 2022, can perform full range necessary synthesis, including multi‐component reactions, cross‐coupling, substitution, cyclization, rearrangement, stereospecific asymmetric α‐Bromocarbonyl have created new trend alkylation, which then had limited reaction patterns focuses how chemistry.

Язык: Английский

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Base-Promoted Formal [3 + 2] Cycloaddition of α-Halohydroxamates with Carbon Disulfide to Synthesize Polysubstituted Rhodanines

Organic Letters, Год журнала: 2022, Номер 24(15), С. 2837 - 2841

Опубликована: Апрель 8, 2022

A concise and practical strategy via potassium-carbonate-mediated [3 + 2]-cycloaddition reaction of α-halohydroxamates with the common solvent carbon disulfide for synthesis functionalized rhodanine derivatives in good to excellent yields is developed. The present methodology features a wide substrate scope as well functional group tolerance. potential synthetic utility this protocol demonstrated by series natural product containing rhodamine skeletons.

Язык: Английский

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(2‐Ethoxy‐2‐oxoethyl)‐dimethyl Sulfonium Bromide

Encyclopedia of Reagents for Organic Synthesis, Год журнала: 2025, Номер unknown, С. 1 - 5

Опубликована: Янв. 3, 2025

image [5187‐82‐6] C 6 H 13 BrO 2 S (MW 229.14) InChI = 1S/C6H13O2S.BrH/c1‐4‐8‐6(7)5‐9(2)3;/h4‐5H2,1‐3H3;1H/q+1;/p‐1 InChIKey JXFPTJYKYKVENJ‐UHFFFAOYSA‐M (used as a stabilized precursor of sulfur ylide reagent for the cycloaddition reaction) Physical Data: mp 86–88 °C. 1 Solubility: soluble in O, insoluble some organic solvents, such hexane. Form Supplied in: white crystalline powder. Analysis Reagent Purity: spectroscopic data: IR v 675, 694, 1133, 1364, 1395, 1525, 1621, 1656, 2923, 2976, 3326 cm −1 and NMR. NMR (400 MHz, CDCl 3 ) δ 4.93 s (2 , SCH ), 4.12 q CH 3.33 [6 (CH S], 1.16 t (3 (100 163.76 (CO), 63.43 (OCH 36.51 (SCH 25.20 [(CH 14.21 ). Preparative Method: solution ethyl bromoacetate acetone or DMSO was stirred under nitrogen, dimethyl sulfide added one portion (eq 1). A precipitate started to appear immediately became thicker upon stirring. After stirring 6–18 h at room temperature, solid filtered, washed with acetone, dried vacuum afford sulfonium salt crystals. Handling, Storage, Precautions: (2‐ethoxy‐2‐oxoethyl) bromide is stable air. The can be stored dry well‐ventilated place should protected from moisture.

Язык: Английский

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Ring opening of donor-acceptor-type cyclopropene unveils electrophilic ketene with vinylogous [4 C + n] periselective cyclization mode

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Апрель 29, 2025

Since its advent 120 years ago, the [2+n] coupling cyclization of ketene has been prevalently used for synthesis N- and O-heterocycles. In contrast, vinylogous version, i.e., use alkenyl as 4 C synthon, remain elusive. We report herein that in rare SN1-type ring-opening electron-deficient cyclopropene, initially formed sp2-carbocation-containing zwitterionic intermediate undergoes facile 1,4-alkoxy migration to generate a functionalized ketene. This electrophilic not only allows challenging N-nucleophiles be engaged conventional reactions (n = 1 ~ 3), also unveiled [4+n] mode, exemplified by [4 + 1] formal 4] construct pyrrolidinone azocine frameworks. The protocol offers unified entry distinct class lactam scaffolds exhibit anti-cancer potential, constituent key natural product scaffold display interesting 1e- 2e- reactivities. work reveals broader synthetic potential SN1 type cyclopropene "dehydro"-donor-acceptor cyclopropane (DDAC) substrate, could have ramifications chemistry, N-heterocyclic chemistry related medicinal research, well donor-acceptor system chemistry.

Язык: Английский

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Synthesis of 2-Azetidinones via Cycloaddition Approaches: An Update

Reactions, Год журнала: 2024, Номер 5(3), С. 492 - 566

Опубликована: Авг. 16, 2024

The present review is a comprehensive update of the synthesis monocyclic β-lactams via cycloaddition reactions. According to IUPAC definition cycloaddition, both elementary and stepwise processes (formal cycloadditions) have been considered. years 2019–2022 are covered by cited literature. focus on synthetic aspects with emphasis structural scope, reaction conditions, mechanistic aspects, selectivity results. Selected significant data related biological activities applications also highlighted.

Язык: Английский

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Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(47)

Опубликована: Окт. 10, 2022

Abstract Aza‐oxyallyl cations, as proposed by Sheehan in the 1960s have garnered significant attention among synthetic organic community, owing to their diverse reactivity profile for constructing N‐scaffolds of biological interest. During its initial growth, aza‐oxyallyl cations were used effectively a 3‐unit synthon 1,3 dipoles create N‐heterocycles via cycloaddition reactions, wherein cation served electrophilic counterpart. Recently, new variations been reported, including usage 1,4 dipole domino and unique alkylating ability heteroatoms. This review article provides an update recent developments this area prevailing mechanistic insight.

Язык: Английский

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Expedient (3+3)-annulation of in situ generated azaoxyallyl cations with diaziridines

Chemical Communications, Год журнала: 2023, Номер 59(53), С. 8270 - 8273

Опубликована: Янв. 1, 2023

Efficient annulation of in situ formed azaoxyallyl cations using a base has been accomplished with diaziridines to provide 1,2,4-triazines at room temperature. The substrate scope, scale up, functional group tolerance and transition-metal free reaction conditions are the important practical features.

Язык: Английский

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