Organocatalytic Asymmetric [3 + 2] Cyclization: Enantioselective Synthesis of α-Indolyl Pyrrolo[1,2-a]indole Scaffolds DOI

Hanxiao Shen,

Kanghua Rui,

Xufeng Lin

et al.

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

Published: Oct. 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

Language: Английский

Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks DOI

Yaopeng Liu,

Qingyu Tian,

Jin Ge

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6246 - 6276

Published: Jan. 1, 2024

Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.

Language: Английский

Citations

12
Organocatalytic asymmetric cascade bicyclization: access to chiral polycyclic bisindoles from 2-indolylmethanols and propargylic alcohols DOI
Wen-Run Zhu, Qiong Su, Xiaoyi Deng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2040 - 2046

Published: Jan. 1, 2024

A chiral phosphoric acid-catalyzed asymmetric bis-cyclization of α-indolyl propargylic alcohols with 2-indolylmethanols was realized.

Language: Английский

Citations

5
Chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes: access to polycyclic indoles DOI
Rui Dong,

Tian‐Jiao Han,

Lihua Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3624 - 3629

Published: Jan. 1, 2024

Reported herein are the chemodivergent (4 + 3) cycloadditions of 2-indolylmethanols with 1,3,5-triazinanes.

Language: Английский

Citations

3
HFIP-Promoted Divergent Cycloadditions of Difluoroenoxysilanes with 2-Indolylmethanols: Synthesis of Fluoro 2H-Pyrano[3,4-b]indoles and gem-Difluoro Cyclopenta[b]indoles DOI

Rongyao Li,

Jing Zhang, Manman Sun

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4610 - 4615

Published: May 23, 2024

An oxa-6π-electrocyclization of difluoroenoxysilanes with diaryl 2-indolylmethanols has been developed. In addition, a rarely reported C3-nucleophilic [3+2] cycloaddition dialkyl disclosed. This divergent approach affording readily available as three-atom and C2 synthons provides rapid access to fluoro 2

Language: Английский

Citations

3
Catalytic asymmetric formal (2 + 3) cycloaddition involving methyl-substituted 2-indolylmethanols DOI
Sijia Liu,

Tian‐Zhen Li,

Ning‐Yi Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4812 - 4819

Published: Jan. 1, 2024

A catalytic asymmetric formal (2 + 3) cycloaddition of methyl-substituted 2-indolylmethanols was established, which delivered various chiral pyrroloindoles in overall high yields with excellent diastereoselectivities and good enantioselectivities.

Language: Английский

Citations

2
Substrate Controlled [3+3] Relay Catalytic Cyclization of α‐(3‐Isoindolinonyl) Propargylic Alcohols with 5‐Aminoisoxazoles DOI

Wenzhe Li,

Min Gao, Min Li

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(6)

Published: March 12, 2024

Abstract Two different skeletons have been constructed by cyclization of α‐(3‐isoindolinonyl) propargylic alcohols with 5‐aminoisoxazoles bearing N ‐substituents under the relay catalysis Brønsted acid and Lewis acid. This method provided spiro‐isoindolinone‐dihydropyridines moderate to high yields (up 99 %) as well isoxazolo[4,5‐b]pyridines in good 86 %). The structures two products were determined X‐ray crystal structural analyses. Moreover, fluorescence testing proved that one exhibited aggregation induced emission (AIE) effect. Finally, control experiments revealed possible reaction mechanism.

Language: Английский

Citations

1
Enantioselective intramolecular tandem cyclization of o-alkynylbenzamides: generation of enantioenriched CF3-containing spiro-isoindolinone-indoles DOI
Wenzhe Li, Min Li, Shuang Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2591 - 2599

Published: Jan. 1, 2024

Enantioselective intramolecular tandem cyclization of dielectrophile–dinucleophile assembled o -alkynylbenzamides provided a variety spiro-isoindolinone-indoles in low to moderate yields with good enantioselectivities.

Language: Английский

Citations

1
Synthesis of Chiral 3H‐pyrrolo[1,2‐a]indoles via Organocatalytic Enantioselective Addition of Alkynyl Biphenyl Quinone Methides DOI

Sheng Pan,

Xing Wang,

Meiwen Liu

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(21)

Published: July 17, 2024

Abstract An organocatalytic enantioselective reaction utilizing α‐[4‐(4‐hydroxyphenyl)phenyl]propargyl alcohols and 3‐substituted indoles has been successfully established for the synthesis of chiral 3 H ‐pyrrolo[1,2‐ a ]indoles. Through assistance an appropriate phosphoric acid, cascade sequence is facilitated, beginning with dehydration to form alkynyl 4,4’‐biphenyl quinone methides ( 4,4’‐BQMs ). Subsequently, 1,12‐addition ]indoles these results in formation allenes, which are then protonated regenerate . Finally, intramolecular annulation occurs smoothly, leading production range high efficiency asymmetric induction.

Language: Английский

Citations

1
Lewis-Acid-Catalyzed (3+2) Annulation of 2-Indolylmethanols with Propargylic Alcohols to Access Cyclopenta[b]indoles DOI Creative Commons
Tengfei Wu,

Z. Fu,

Yi‐Rui Zhang

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(6), P. 1251 - 1251

Published: March 12, 2024

Herein, a Sc(OTf)3-catalyzed (3+2) annulation of 2-indolylmethanols with propargylic alcohols is reported. The reaction proceeds via Friedel–Crafts-type allenylation/5-exo-annulation cascade. In the reaction, 2-indolylmethanol used as three-carbon synthon, and propargyl alcohol two-carbon synthon. This method provides direct high-yield pathway for synthetically useful cyclopenta[b]indoles. general, features easily accessible substrates broad scope generality, formation multiple bonds high efficiency, easy scale-up.

Language: Английский

Citations

0
In(OTf)3-Catalyzed Formal (4 + 3) Cycloaddition Reactions of 3-Benzylideneindoline-2-thiones with 2-Indolylmethanols DOI

Xuelong Wang,

Yi Yang, Yan Jiang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5902 - 5906

Published: Jan. 1, 2024

We report the In(OTf)

Language: Английский

Citations

0