Rh(III)-Catalyzed C–H Activation of Benzamides and Chemodivergent Annulation with Benzoxazinanones: Substrate Controlled Selectivity DOI

Danqing Ji,

Xingwei Li

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7083 - 7088

Published: Sept. 25, 2023

Decarboxylative annulation of propargyl carbamates with benzamides has been realized via rhodium-catalyzed C-H bond activation under mild conditions, delivering two distinct classes heterocycles in high efficiency and selectivity substrate control. This protocol provides a direct synthetic method for the preparation functionalized 1,8-naphthyridines isoindolinones.

Language: Английский

Photocatalytic Bicyclization of Indole-Tethered 1,6-Enynes for Diastereoselective Synthesis of Pyrrolo[3,2,1-jk]carbazoles DOI
Hang‐Dong Zuo, Xi Chen,

Ya‐Yu Yuan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3810 - 3815

Published: April 28, 2024

A visible-light-driven photocatalytic protocol is established for the diastereoselective synthesis of pyrrolo[3,2,1-jk]carbazoles via a radical-triggered multicomponent bicyclization reaction starting from readily available indole-tethered 1,6-enynes and α-benzyl-α-bromomalonates under mild conditions. This approach exhibits wide substrate compatibility excellent tolerability toward various functional groups boasts benefit efficient ring formation chemical bond creation.

Language: Английский

Citations

6
Modular Synthesis of Planar-Chiral Cyclononenes via trans-Retentive Trapping of π-Allyl-Pd Dipoles DOI
Zheng‐Xin Zhou,

Yue-Liu-Ting Fu,

Chen Zhang

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 17, 2025

Trans-cycloalkenes are abundant in bioactive natural products and have been used as powerful tools chemical biology drug discovery. However, strategies for the modular synthesis of trans-cycloalkenes, especially planar-chiral medium-sized ones, with high efficiency selectivity, still remain elusive. Herein, we report a Pd-catalyzed asymmetric [7 + 2] cyclization strategy to address this challenge. As result, two types trans-cyclononenes bearing all-carbon chiral quaternary stereocenters produced up 85% yield, >99% ee, >19:1 dr (42 examples). The key success is maintenance trans-2H configuration π-allyl-Pd species along unusual linear selectivity during H-bond-assisted process. In addition, conversion planar chirality central its application selective bioimaging cancer cells via bioorthogonal reaction were performed demonstrate synthetic value methodology.

Language: Английский

Citations

0
Pd-Catalyzed [4 + 1] Annulation Strategy to Functionalized 4-Methyleneproline Derivatives DOI Creative Commons
Jiaxin Han,

Wenzheng Gao,

Joseph P. A. Harrity

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1552 - 1555

Published: Jan. 23, 2024

A Pd-catalyzed formal [4 + 1] cycloaddition reaction of sulfur ylides and in situ-generated Pd-stabilized zwitterions offers a convenient route to series functionalized proline derivatives. The utility this method is demonstrated by gram-scale synthesis chemoselective functionalization proline-based derivative.

Language: Английский

Citations

3
Recent Advances in Palladium-Catalyzed [4 + n] Cycloaddition of Lactones, Benzoxazinanones, Allylic Carbonates, and Vinyloxetanes DOI
Mengyan Guo, Panke Zhang, Er‐Qing Li

et al.

Topics in Current Chemistry, Journal Year: 2023, Volume and Issue: 381(6)

Published: Nov. 3, 2023

Language: Английский

Citations

9
Advancements in Asymmetric Catalytic Approaches Involving Benzoxazinone Derivatives DOI Open Access
Ruilin Zhang,

Kaixiong Qiu,

Hongfei Gao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(17), P. 2767 - 2788

Published: July 10, 2023

Abstract Chiral aza ‐heterocycles, as a sort of key frameworks natural products et al , are deeply concerned by synthetic chemists. In recent years, catalytic asymmetric reactions several types zwitterionic intermediates, originating form benzoxazinone derivatives, have become popular and efficient approach to obtain chiral ‐heterocycles. Given that, this review attempts summarize development in the field derivatives powerful dipole precursors for construction past various their been developed. Herein, is organized display important potentials values.

Language: Английский

Citations

7
Ligand-Controlled Diastereodivergency in Propargylic Alkylation of Vinylogous Aza-Enamines: Construction of 1,3-Stereocenters DOI
Suman Ghosh, Santanu Mukherjee

Organic Letters, Journal Year: 2023, Volume and Issue: 25(40), P. 7304 - 7309

Published: Oct. 2, 2023

The first diastereodivergent propargylic alkylation reaction is developed. This Cu(I)-catalyzed formal decarboxylative [4+2] cycloaddition between ethynyl benzoxazinanone and vinylogous aza-enamine delivers each diastereomer of tetrahydroquinoline derivatives, bearing 1,3-stereocenters, using either i-Pr-Pybox or BINAP as the ligand under otherwise identical conditions. application aza-enamines in a transition metal-catalyzed transformation example creation 1,3-stereocenters substitution reaction.

Language: Английский

Citations

4
Synthetic strategies for the construction of C3–N1′ bisindoles DOI
Takumi Abe

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(9), P. 1756 - 1764

Published: Jan. 1, 2024

C3-N1' bisindoles are unique structures, and the construction of these structures has drawn much attention. However, their synthesis still presents significant challenges that limit functional group compatibility. This minireview summarizes recent progress in methodology for constructing bisindoles. There two approaches access to bisindoles: (1) direct including reverse polarity techniques. (2) Stepwise using designed prefunctionalized substrates enable further functionalization by additional reactions facilitate target products. I believe this review will allow its readers develop novel

Language: Английский

Citations

1
Copper-catalyzed reaction of benzoxazinanones with sulfilimines: access to 2-ethynyl-benzoimidazoles via an abnormal skeletal rearrangement DOI
Tao Zhang,

Yifeng Ni,

Jiangtao Sun

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(22), P. 4583 - 4586

Published: Jan. 1, 2023

A copper-catalyzed reaction of benzoxazinanones with sulfilimines has been described, and 2-ethynyl-benzoimidazoles were obtained in good yields via an abnormal skeletal rearrangement.

Language: Английский

Citations

2
Copper‐Catalyzed α,β‐Regioselective (2+4) Cycloaddition of Propargylic Esters DOI

Guo‐Ke Zhang,

Shufang Wu, Zhong Chen

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(46)

Published: Sept. 26, 2023

Abstract A copper‐catalyzed α,β‐regioselective (2+4) cycloaddition of propargylic esters with o ‐hydroxyphenyl substituted secondary phosphine oxides (SPOs) was established, which afforded a series phosphorus‐containing six‐membered heterocycles in high yields. This reaction represents the first (2+n) via intermediates copper‐allenylidenes, will enrich chemistry and copper‐allenylidenes. Moreover, this work also application SPOs as 1,4‐dinucleophiles cycloadditions, provides useful protocol for synthesis potential bioactivity.

Language: Английский

Citations

2
Dearomatization-Rearomatization Reaction of Metal-Polarized Aza-ortho-quinone Methides DOI Open Access
Jian Zhang, Weiping Deng

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(8), P. 2980 - 2980

Published: Jan. 1, 2023

Language: Английский

Citations

1