Asymmetric Synthesis of Spiro[3,2′-morpholine-oxindoles] Derivatives via the [5 + 1] Annulation Reaction DOI
Dongyang Sun, Heng Zhang,

Jigang Gao

и другие.

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(23), С. 16815 - 16823

Опубликована: Ноя. 11, 2021

An efficacious method in which BINOL-type chiral imidodiphosphoric acid catalyzed the asymmetric [5 + 1] annulation reaction of 2-pyrrolylphenol with 1-methylindoline-2,3-dione was established. The strategy tolerated a broad substrate scope, and 30 examples were obtained. A range enantioenriched spiro[3,2′-morpholine-oxindole] derivatives incorporate tertiary stereocenter, moderate to excellent yields (up 96%) enantioselectivities 99%) under mild conditions, delivered.

Язык: Английский

Synthesis of Cyclopenta[b]indoles via Rhodium‐Catalyzed Cascade Migration‐Annulation of 1‐Sulfonyl‐1,2,3‐triazoles and Indoles DOI
Huaping Xu, Heng Wang, Ze‐Feng Xu

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(10), С. 1623 - 1628

Опубликована: Май 5, 2023

Abstract A rhodium‐catalyzed cascade 1,3‐sulfinate migration, intermolecular [3+2] annulation of 1‐sulfonyl‐1,2,3‐triazoles and indoles was achieved. The one‐pot protocol provided a method to construct cyclopenta[ b ]indoles bearing four stereocenters in 45% 99% yields with 1.6:1 >20:1 diastereoselectivities. In addition, could be transformed into variety functionalized compounds, demonstrating the synthetic value this migration‐annulation strategy ring system synthesis. magnified image

Язык: Английский

Процитировано

7

Construction of cyclopenta[b]dihydronaphthofurans via TsOH-catalyzed consecutive biscyclization of dithioallylic alcohols and 1-styrylnaphthols DOI
Heping Li,

Xiaoling Wu,

Gu Zhan

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(16), С. 2275 - 2278

Опубликована: Янв. 1, 2023

An efficient TsOH-catalyzed consecutive biscyclization cascade reaction of dithioallylic alcohols with 1-styrylnaphthols is demonstrated for the concise construction pharmaceutically important cyclopenta[b]dihydrobenzofuran scaffolds. This process involved an acid-catalyzed (3+2) cycloaddition followed by intramolecular nucleophilic addition, providing cyclopenta[b]dihydronaphthofurans bearing a tetra- or fully substituted cyclopentane core in good yields exclusive diastereoselectivities (>20 : 1 d.r.).

Язык: Английский

Процитировано

6

Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds DOI
Wei Wu,

Na Liao,

Qi Wei

и другие.

Organic Letters, Год журнала: 2021, Номер 23(17), С. 6872 - 6876

Опубликована: Авг. 25, 2021

An efficient asymmetric tandem reaction of o-alkynylbenzaldehydes, amines, and diazo compounds catalyzed by chiral silver imidodiphosphate has been established. Chiral 1,2-dihydroisoquinoline analogues have a tertiary stereocenter at the C1 position, substituents C3 position are available with up to 97% yields 98% ee. These products can be elaborated into corresponding β-aminophosphonates or PARP1-inhibitor analogues.

Язык: Английский

Процитировано

13

Construction of diverse spirooxindoles via a domino reaction of arylamines, but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones DOI

Lingyun Zhu,

Jing Sun,

Dan Liu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(47), С. 9392 - 9397

Опубликована: Янв. 1, 2023

An iodine-promoted domino reaction of arylamines/benzylamines, dialkyl but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones showed very interesting molecular diversity. The in acetonitrile at 65 °C the presence 30% mmol I2 resulted spiro[indoline-3,1'-pyrido[4,3-b]indoles] satisfactory yields. When anilines without para-substituents were used reaction, a direct substitution hydroxyl group to 2-(phenylamino)maleate para-position aniline gave chain products good Additionally, similar reactions with benzylamines not only spiro[indoline-3,1'-pyrido[4,3-b]indoles], but also afforded spiro[indoline-3,1'-pyrano[4,3-b]indol]-2-ones lower A plausible annulation mechanism was rationally proposed for formation different kinds polycyclic compounds.

Язык: Английский

Процитировано

3

Lewis acid-catalyzed [3 + 2] annulations of oxindole based spirocyclic donor–acceptor cyclopropanes with ynamides DOI
Dongxin Zhang,

Qihang Cheng,

Lvjia Chen

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(44), С. 9645 - 9648

Опубликована: Янв. 1, 2021

[3 + 2] annulations of spirocyclopropyl oxindoles with ynamides to offer biologically important spirocyclopenteneoxindoles in high yields good diastereoselectivities were developed.

Язык: Английский

Процитировано

7

Imidodiphosphoric Acids Catalysed Asymmetric Functionaliza‐tion with Thiols: Access to Oxindole Derived ɑ‐Chiral Thioethers DOI

Xiangshuo Qin,

Guofeng Jiang,

Jigang Gao

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 364(1), С. 225 - 231

Опубликована: Ноя. 9, 2021

Abstract Chiral imidodiphosphoric acid‐catalysed asymmetric functionalization of 3‐hydroxy bisindoles was established. Sulfur‐containing groups could be successfully introduced into isatin frameworks using commercially available thiols. The transformation compatible with substrates bearing distinct substituents, both aromatic and aliphatic thiols were amenable to afford the desired products. A total 41 reactions furnished various chiral 3‐thiooxindoles in 23%–99% yield, 72%–99% enantioselectivity. magnified image

Язык: Английский

Процитировано

2

Asymmetric Synthesis of Spiro[3,2′-morpholine-oxindoles] Derivatives via the [5 + 1] Annulation Reaction DOI
Dongyang Sun, Heng Zhang,

Jigang Gao

и другие.

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(23), С. 16815 - 16823

Опубликована: Ноя. 11, 2021

An efficacious method in which BINOL-type chiral imidodiphosphoric acid catalyzed the asymmetric [5 + 1] annulation reaction of 2-pyrrolylphenol with 1-methylindoline-2,3-dione was established. The strategy tolerated a broad substrate scope, and 30 examples were obtained. A range enantioenriched spiro[3,2′-morpholine-oxindole] derivatives incorporate tertiary stereocenter, moderate to excellent yields (up 96%) enantioselectivities 99%) under mild conditions, delivered.

Язык: Английский

Процитировано

2