Design and Catalytic Asymmetric Synthesis of Furan‐Indole Compounds Bearing both Axial and Central Chirality DOI
Jing‐Yi Wang,

Cong‐Hui Gao,

Cheng Ma

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(8)

Published: Dec. 29, 2023

Abstract In the chemistry community, catalytic asymmetric synthesis of furan‐based compounds bearing both axial and central chirality has proven to be a significant but challenging issue owing importance difficulty in constructing such frameworks. this work, we have realized first five‐five‐membered via organocatalytic (2+4) annulation achiral furan‐indoles with 2,3‐indolyldimethanols uncommon regioselectivity. By strategy, furan‐indole were synthesized high yields excellent regio‐, diastereo‐, enantioselectivities. Moreover, theoretical calculations conducted provide an in‐depth understanding reaction pathway, activation mode, origin selectivity.

Language: Английский

Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality DOI Creative Commons
Shuang Yang,

Jia-Bo Huang,

Dahua Wang

et al.

Precision Chemistry, Journal Year: 2024, Volume and Issue: 2(5), P. 208 - 220

Published: April 23, 2024

The catalytic asymmetric diastereodivergent synthesis of axially chiral 2-alkenylindoles was established via phosphoric acid-catalyzed addition reactions C3-unsubstituted with

Language: Английский

Citations

17
Atroposelective Construction of Axially Chiral Alkene‐Indole Scaffolds via Catalytic Enantioselective Addition Reaction of 3‐Alkynyl‐2‐indolylmethanols† DOI
Jing‐Yi Wang, Meng Sun,

Xian‐Yang Yu

et al.

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 39(8), P. 2163 - 2171

Published: April 29, 2021

Main observation and conclusion Atroposelective construction of axially chiral alkene‐heteroaryl scaffolds is highly desired but challenging. In this work, we established an atroposelective alkene‐indole via the strategy catalytic enantioselective addition reaction 3‐alkynyl‐2‐indolylmethanols with bulky nucleophiles. strategy, α‐amido sulfones were used as competent nucleophiles phosphoric acid (CPA) acted suitable catalyst for reaction. By a new class acyclic alkene‐indoles was synthesized in overall high yields (up to 86%), excellent ( E / Z )‐selectivity (all > 95 : 5) good enantioselectivities 92 8 er). This represents first frameworks, which will add member family atropoisomeric heterocycles, especially indole compounds.

Language: Английский

Citations

78
Asymmetric synthesis of N–N axially chiral compounds via organocatalytic atroposelective N-acylation DOI Creative Commons
Wei Lin, Qun Zhao, Yao Li

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 13(1), P. 141 - 148

Published: Nov. 24, 2021

A highly efficient atroposelective N -acylation reaction of quinazolinone type benzamides with cinnamic anhydrides for the direct catalytic synthesis optically active atropisomeric derivatives was developed.

Language: Английский

Citations

71
Advances in Catalytic Asymmetric Reactions Using 2-Indolylmethanols as Platform Molecules DOI Open Access
Hong‐Hao Zhang, Feng Shi

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(10), P. 3351 - 3351

Published: Jan. 1, 2022

Indole-based chiral heterocycles constitute a class of important heterocyclic compounds that are found in numerous natural products, pharmaceuticals, pesticide, and functional materials.The efficient highly enantioselective synthesis indole derivatives has become one the most issues organic chemistry.Due to simple reactivity traditional indoles, their involved catalytic asymmetric reactions very limited, resulting limited types constructed indole-based frameworks.To solve these challenging issues, chemists devised strategy introducing groups ring, so as obtain series functionalized derivatives, namely platform molecules, building blocks for constructing indole-related frameworks.Among them, 2-indolylmethanols which were designed on consideration introduction hydroxymethyl group C2-position ring would change reactive site ring.This molecules can act either electrophiles or nucleophiles, multi-carbon reactions.Therefore, design development have provided new derivatives.The advances using summarized, will open window designing application molecules.

Language: Английский

Citations

68
Rational Design of Axially Chiral Styrene‐Based Organocatalysts and Their Application in Catalytic Asymmetric (2+4) Cyclizations DOI

Si‐Jia Liu,

Zhi‐Han Chen,

Jiayi Chen

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(7)

Published: Nov. 30, 2021

A new class of axially chiral styrene-based thiourea tertiary amine catalysts, which have unique characteristics such as an efficient synthetic route, multiple elements, and activating groups, has been rationally designed. These catalysts proven to be organocatalysts, enabling the chemo-, diastereo-, enantioselective (2+4) cyclization 2-benzothiazolimines with homophthalic anhydrides in good yields (up 96 %) excellent stereoselectivities (all >95:5 dr, up 98 % ee). More importantly, theoretical calculations elucidated important role styrene moiety controlling both reactivity enantioselectivity. This work not only represents first design catalytic asymmetric 2-benzothiazolimines, but also gives in-depth understanding organocatalysts.

Language: Английский

Citations

65
Nitrosobenzene‐Enabled Chiral Phosphoric Acid Catalyzed Enantioselective Construction of Atropisomeric N‐Arylbenzimidazoles DOI

Qian‐Jin An,

Xia Wang, Wei‐Yi Ding

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(47), P. 24888 - 24893

Published: Sept. 23, 2021

Abstract Described herein is an imidazole ring formation strategy for the synthesis of axially chiral N‐arylbenzimidazoles by means phosphoric acid catalysis. Two sets conditions were developed to transform two classes 2‐naphthylamine derivatives into structurally diverse N‐arylbenzimidazole atropisomers with excellent chemo‐ and regioselectivity as well high levels enantiocontrol. It worth reflecting on unique roles played nitroso group in this domino reaction. functions a linchpin first offering electrophilic site (N) initial C−N bond while resulting amine performs nucleophilic addition form second bond. Additionally, it could facilitate final oxidative aromatization oxidant. The atropisomeric products be conveniently elaborated series derivatives, enabling exploitation their potential utilities asymmetric

Language: Английский

Citations

61
Design and synthesis of axially chiral aryl-pyrroloindoles via the strategy of organocatalytic asymmetric (2 + 3) cyclization DOI Creative Commons
Ping Wu, Lei Yu,

Cong‐Hui Gao

et al.

Fundamental Research, Journal Year: 2022, Volume and Issue: 3(2), P. 237 - 248

Published: Jan. 21, 2022

The catalytic asymmetric construction of axially chiral indole-based frameworks is an important area research due to the unique characteristics such frameworks. Nevertheless, in this still its infancy and has some challenges, as designing constructing new classes scaffolds developing their applications catalysts, ligands, etc. To overcome these we present herein design atroposelective synthesis aryl-pyrroloindoles a class via strategy organocatalytic (2 + 3) cyclization between 3-arylindoles propargylic alcohols. More importantly, was derived into phosphines, which served efficient ligands palladium-catalyzed reactions. Moreover, theoretical calculations provided in-depth understanding reaction mechanism. This work offers for scaffolds, are promising finding more catalysis.

Language: Английский

Citations

59
Recent advances in the catalytic asymmetric construction of atropisomers by central-to-axial chirality transfer DOI

Xiao-Long Min,

Xiulian Zhang, Rui Shen

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(8), P. 2280 - 2292

Published: Jan. 1, 2022

We highlighted the recent advances in field of central-to-axial chirality transfer for synthesis axially chiral molecules.

Language: Английский

Citations

55
Atroposelective Construction of Nine‐Membered Carbonate‐Bridged Biaryls DOI
Shiqi Jia,

Yuhong Tian,

Xin Li

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(31)

Published: May 27, 2022

Abstract We herein demonstrated an efficient method for the atroposelective construction of nine‐membered carbonate‐bridged biaryls through vinylidene ortho ‐quinone methide (VQM) intermediates. Diverse products with desirable pharmacological features were synthesized in satisfying yields and good to excellent enantioselectivities. In subsequent bioassays, several agents showed considerable antiproliferative activity via mitochondrial‐related apoptosis mechanism. Further transformations produced more structural diversity may inspire new ideas developing functional molecules.

Language: Английский

Citations

52
Design and Application of m‐Hydroxybenzyl Alcohols in Regioselective (3 + 3) Cycloadditions of 2‐Indolymethanols† DOI

Yi‐Cheng Shi,

Xinyu Yan, Ping Wu

et al.

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 41(1), P. 27 - 36

Published: Sept. 16, 2022

Comprehensive Summary A new class of m ‐hydroxybenzyl alcohols has been designed as competent three‐carbon building blocks and achieved their application in 2‐indolylmethanol‐involved regioselective (3 + 3) cycloadditions under the catalysis Brønsted acids. By this appoach, a series indole‐fused six‐membered cycloadducts have synthesized overall good yields (up to 98%) with excellent regioselectivity (all >95: 5 rr), thus affording powerful method for construction rings. Moreover, catalytic asymmetric version cycloaddition preliminarily investigated, which revealed potential reaction constructing chiral rings an enantioselective manner. This work not only accomplished first design reactants, but also represents cycloadditions. In addition, provides example C3‐nucleophilic 2‐indolylmethanols, will substantially enrich chemistry 2‐indolylmethanols.

Language: Английский

Citations

52