The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Окт. 26, 2024
A novel asymmetric [3 + 2] cyclization of α-indolyl propargylic alcohols with 3-alkyl-1H-indoles via chiral phosphoric acid catalysis has been established. This strategy allowed the synthesis pyrrolo[1,2-a]indole derivatives high yields (up to 91%) and excellent enantioselectivities 99% ee), facilitating both reaction activity enantioselectivity by using solvent CH
Язык: Английский
The Journal of Organic Chemistry, Год журнала: 2022, Номер 88(12), С. 7684 - 7702
Опубликована: Ноя. 23, 2022
An axially chiral indolyl-pyrroloindole scaffold, a new member of indole-based scaffolds, has been designed, and the catalytic asymmetric construction this scaffold established by strategy organocatalytic (2 + 3) cycloaddition 3,3'-bisindoles with isoindolinone-based propargylic alcohols. By approach, series derivatives bearing both axial chirality central were synthesized in high yields excellent diastereo- enantioselectivities (up to 95% yield, 91:9 dr, 99% ee). This reaction not only realizes first n) as 1,2-dinucleophiles but also provides for atroposelective scaffolds five-five-membered rings, thus solving challenges constructing class scaffolds.
Язык: Английский
Процитировано
37
Organic Chemistry Frontiers, Год журнала: 2022, Номер 10(1), С. 30 - 34
Опубликована: Ноя. 14, 2022
Organocatalytic enantioselective construction of chiral spiro N , -acetal carbon stereocenters and axially 3-arylindoles has been achieved in one pot.
Язык: Английский
Процитировано
27
Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(14), С. 3662 - 3668
Опубликована: Янв. 1, 2023
With the aid of chiral phosphoric acid, enantioselective 1,6-addition tryptamines to in situ formed alkynyl 7-methylene-7 H -indoles from tertiary α-(7-indolyl)methanols has been established, furnishing axially tetrasubstituted allenes high yields.
Язык: Английский
Процитировано
16
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2794 - 2799
Опубликована: Янв. 31, 2024
A Brønsted acid catalyzed aza-Friedel–Crafts reaction of indolizines with 3-hydroxyisoindolinones has been established, which constructs isoindolinone derivatives bearing a tetrasubstituted stereocenter in good to high yields and enantioselectivities. Notably, this strategy provides new access C1-functionalization excellent regioselectivities. Moreover, intriguing C1-regioselective transformation was induced under thermodynamic control.
Язык: Английский
Процитировано
6
Organic Letters, Год журнала: 2024, Номер 26(23), С. 4932 - 4937
Опубликована: Июнь 3, 2024
Herein we report the first use of p-quinone diimide for aminative dearomatization 2,3-disubstituted indoles to furnish C3 aza-quaternary chiral indolenines. This approach, which proceeds via an electrophilic 1,6-addition diimide, allows synthesis array optically active indolenines with high yields and excellent enantioselectivities. A one-pot approach same has also been established further improve synthetic accessibility this protocol.
Язык: Английский
Процитировано
6
Organic Letters, Год журнала: 2023, Номер 25(36), С. 6654 - 6658
Опубликована: Сен. 6, 2023
A novel chiral phosphoric acid-catalyzed tandem regioselective 1,6-addition/double intramolecular nucleophilic addition annulation of the propargylic 3-methyleneindoles in situ generated from α-indolyl alcohols with 2-indolylmethanols has been developed. The methodology afforded new trifluoromethyl pentalenobisindoles bearing an all-carbon quaternary stereogenic center generally good yields excellent enantioselectivities.
Язык: Английский
Процитировано
12
Organic Letters, Год журнала: 2022, Номер 24(25), С. 4699 - 4703
Опубликована: Июнь 21, 2022
Developed herein is an enantioselective Friedel–Crafts alkylation reaction of N-unprotected alkynyl trifluoromethyl ketimines with pyrroles catalyzed by chiral phosphoric acid to furnish primary α-trifluoromethyl-α-(2-pyrrolyl)propargylamines high enantioselectivity. Transformation the group adducts afforded optically active α-trifluoromethylated amines bearing various substituents such as alkyl, alkenyl, enyne, and triazole without loss optical purity.
Язык: Английский
Процитировано
16
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 17438 - 17449
Опубликована: Дек. 6, 2023
Herein, we disclose the first report on Ru(II)-catalyzed amidation/thioamidation of 3-hydroxy-3-arylisoindolinones with isocyanates/isothiocyanates, respectively. The reaction furnishes spiroisoindolinones via sequential C-H functionalization ortho bond followed by intramolecular cyclization in moderate to high yields (up 94%). Moreover, developed strategy is highly atom-economical and site-selective shows diverse substrate generality. Also, synthesized undergo several chemical transformations.
Язык: Английский
Процитировано
9
Organic Letters, Год журнала: 2024, Номер 26(11), С. 2321 - 2325
Опубликована: Март 11, 2024
A highly diastereoselective synthesis of spiroisoindolinones from enamides and 3-hydroxy-isoindolinones is reported. The reaction proceeds rapidly in the presence p-toluenesulfonic acid as a Brønsted catalyst affords variety densely substituted with three contiguous stereogenic centers high yields (≤98%) diastereoselectivities (up to dr >98:<2:0:0).
Язык: Английский
Процитировано
3
Organic Letters, Год журнала: 2024, Номер 26(36), С. 7667 - 7671
Опубликована: Авг. 29, 2024
A chiral Brønsted acid catalyzed asymmetric aza-Piancatelli rearrangement of 3-furyl-3-hydroxyisoindolinones with anilines has been developed, enabling the divergent construction spiro-cyclopentenone-isoindolinones in high yields excellent diastereo- and enantioselectivities even under a low catalyst loading 0.5 mol%.
Язык: Английский
Процитировано
3