Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles DOI

Lunfeng Chen,

Pengfei Li

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation Morita-Baylis-Hillman carbonates, organocatalytic dearomatization afforded an array enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34-79% yields with 61-91% ee. With Boc

Language: Английский

Chiral phosphoric acid-catalyzed transfer hydrogenation of 3,3-difluoro-3H-indoles DOI Creative Commons
Yumei Wang, Guangzhu Wang, Yanping Zhu

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 205 - 211

Published: Feb. 1, 2024

A convenient and efficient method for the synthesis of optically active difluoro-substituted indoline derivatives starting from corresponding 3 H -indoles by chiral phosphoric acid-catalyzed transfer hydrogenation was developed. Using Hantzsch ester as hydrogen source under mild reaction conditions, target products can be obtained with excellent yield enantioselectivity.

Language: Английский

Citations

2
Asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes by nickel catalysis DOI

Xinmiao Huang,

Xin Tan, Xu Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(23), P. 5940 - 5949

Published: Jan. 1, 2023

Herein, we report an asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes enabled by nickel catalysis to access structurally diverse gem -difluorovinyl-containing chiral polycyclic indolines.

Language: Английский

Citations

4
Dearomative spiroannulation of indoles enabled by the diaza-[1,2]-Wittig rearrangement DOI

Can Luo,

Chun-Yan Guan,

Zhenyu Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1685 - 1691

Published: Jan. 1, 2024

Reported herein is the first diaza-[1,2]-Wittig rearrangement-enabled dearomative spiroannulation reaction of indoles. This protocol features metal-free conditions, a redox-neutral process, broad substrate scope, and good yield.

Language: Английский

Citations

1
Switchable divergent synthesis of chiral indole derivatives via catalytic asymmetric dearomatization of 2,3-disubstituted indoles DOI Creative Commons
Tingting Liu,

Jianbin Wang,

Rou Xiao

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(22), P. 15591 - 15596

Published: Jan. 1, 2024

A strategy allowing the switchable divergent synthesis of chiral indole derivatives was established via phosphoric acid-catalyzed asymmetric dearomatization 2,3-disubstituted indoles using naphthoquinone monoimines as electrophiles. The products were switched between indolenines and fused indolines according to post-processing conditions. Both two types obtained in good high yields with generally excellent enantioselectivities. NaBH4 found work a promoter well reductant cyclization process leading indolines.

Language: Английский

Citations

0
Trifluoroacetic Acid Promotes Umpolung of 2‐Methylindole to Achieve C(sp3)‐H Activation DOI

Hongmei Kong,

Kuo Li, Jingfa Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract An umpolung strategy for the C( sp 3 )−H aminomethylation of 2‐methylindole has been developed using trifluoroacetic acid to induce transformation, with aminals serving as precursors iminium ion. Mechanistic studies have clearly shown that may play a pivotal role in this strategy. The utilization readily available starting materials, mild reaction conditions, tolerance complex functional groups, combine yields up 98% and potential biological applications render protocol applicable useful organic synthesis medicinal chemistry.

Language: Английский

Citations

0
Site Specific C3‐Alkenylation of Indoles Mediated by in situ C‐H Iodination DOI
Yongli Zhao,

Dingsheng Cao,

Jie‐Ping Wan

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract The C3‐alkenylation of indoles have been developed by means a novel in situ iodination tactic which is capable mediating the Heck coupling with alkenes. method features specific site‐selectivity oriented C−I bond, high‐step efficiency without pre‐functionalization for C‐halogen bond construction, as well highly general tolerance to different terminal alkenes, including unactivated acrylates, acrylic acid, vinyl sulfone functionalized natural products.

Language: Английский

Citations

0
Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles DOI

Lunfeng Chen,

Pengfei Li

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation Morita-Baylis-Hillman carbonates, organocatalytic dearomatization afforded an array enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34-79% yields with 61-91% ee. With Boc

Language: Английский

Citations

0