Direct synthesis of spirooxindoles enabled by palladium-catalyzed allylic alkylation and DBU-mediated cyclization: concept, scope and applications DOI

Fen Tan,

Xiaoyu He,

Qiao-Qiao Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5443 - 5453

Published: Jan. 1, 2024

A concise construction of spiro[indoline-3,2′-pyrrol]-2-one skeletons is reported. This reaction proceeded through a palladium-catalyzed decarboxylative allylic alkylation followed by DBU-mediated intramolecular cyclization.

Language: Английский

Azidobenziodazolones as Azido Sources for the Enantioselective Copper-Catalyzed Azidation of N-Unprotected 3-Trifluoromethylated Oxindoles DOI
Yuxuan Chen,

Tao Huo,

Quan Yin

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(15), P. 2739 - 2744

Published: April 12, 2023

Both azido (N3) and trifluoromethyl (CF3) groups are key moieties of numerous valuable molecules that extensively applied in drug discovery, chemical biology, synthetic chemistry. However, the asymmetric construction chiral quaternary stereocenters bearing both N3 CF3 is still unexplored. Herein, we report a kind bench-stable easily adjustable benziodazolone-based azidating reagents. These reagents were used to achieve an enantioselective copper-catalyzed azidation N-unprotected 3-trifluoromethylated oxindoles provide diverse enantioenriched 3-N3-3-CF3 oxindoles.

Language: Английский

Citations

12
Fischer's base-triggered formal (3+2) cycloadditions with 3-isothiocyanato oxindoles as acceptor–donor synthons DOI
Xiong-Wei Liu,

Zi‐Yue Chen,

Ren-Ming Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(31), P. 4652 - 4655

Published: Jan. 1, 2023

Herein, previously unreported Fischer's base reactants serving as useful 2C building blocks in (3+2) cycloaddition reactions to build a library of bispiro[Fischer's base-oxindole] hybrids are described. These structurally intriguing products containing three adjacent quaternary stereocentres were smoothly afforded up 82% yield and >20 : 1 dr under catalyst-free conditions. Notably, the present protocol firstly employs 3-isothiocyanato oxindole an acceptor then donor formal cycloadditions, allowing practical, straightforward access diverse cycloadducts. This work expands applicability scope oxindoles, which have been limited behaving donor/acceptor-based synthons cycloadditions previous work.

Language: Английский

Citations

2
Trimethylindolenines as C–N synthons for the assembly of spiro[oxindole-thioxoimidazolidine-indoline] hybrids in formal [3+2] cycloadditions DOI
Wenhui Zhang,

Zi‐Yue Chen,

Ren-Ming Liu

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(26), P. 12296 - 12303

Published: Jan. 1, 2023

This is the first example of trimethylindolenines serving as useful C–N synthons in [3+2] cycloaddition reactions.

Language: Английский

Citations

1
Organocatalyzed enantioselective synthesis of spirooxindole scaffolds DOI
Mohamed S. H. Salem,

Ahmed Gabr,

Meghna Sasi

et al.

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 181 - 217

Published: Jan. 1, 2024

Language: Английский

Citations

0
Direct synthesis of spirooxindoles enabled by palladium-catalyzed allylic alkylation and DBU-mediated cyclization: concept, scope and applications DOI

Fen Tan,

Xiaoyu He,

Qiao-Qiao Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5443 - 5453

Published: Jan. 1, 2024

A concise construction of spiro[indoline-3,2′-pyrrol]-2-one skeletons is reported. This reaction proceeded through a palladium-catalyzed decarboxylative allylic alkylation followed by DBU-mediated intramolecular cyclization.

Language: Английский

Citations

0