Diastereo- and Enantioselective Synthesis of Eight-Membered N-Heterocycles from Benzofuran-Derived Azadienes and Ynones DOI

Suo‐Suo Qi,

Jia-Yi Dong,

Xiaoping Sun

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(2), С. 975 - 985

Опубликована: Янв. 5, 2024

Enantioselective synthesis of eight-membered N-heterocycles represents a long-standing challenge in organic synthesis. Here, by combining the squaramide and DBU catalysis, sequential asymmetric conjugate addition/cyclization reaction between benzofuran-derived azadienes ynones has been well-developed, providing straightforward access to chiral high yields with stereoselectivities. This protocol features use bifunctional catalyst for controlling enantioselectivity products, while is utilized achieve intramolecular cyclization improve diastereoselectivity products.

Язык: Английский

Progress in organocatalytic asymmetric (4+3) cycloadditions for the enantioselective construction of seven-membered rings DOI
Wei Tan, Jiayi Zhang,

Cong‐Hui Gao

и другие.

Science China Chemistry, Год журнала: 2023, Номер 66(4), С. 966 - 992

Опубликована: Фев. 15, 2023

Язык: Английский

Процитировано

82

Asymmetric (4+n) Cycloadditions of Indolyldimethanols for the Synthesis of Enantioenriched Indole‐Fused Rings DOI
Jiayi Zhang, Jiayi Chen,

Cong‐Hui Gao

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(37)

Опубликована: Июнь 24, 2023

Catalytic asymmetric construction of chiral indole-fused rings has become an important issue in the chemical community because significance such scaffolds. In this work, we have accomplished first catalytic (4+2) and (4+3) cycloadditions 2,3-indolyldimethanols by using indoles 2-naphthols as suitable reaction partners under catalysis phosphoric acids, constructing enantioenriched six-membered seven-membered high yields with excellent enantioselectivities. addition, approach is used to realize enantioselective challenging tetrahydroindolocarbazole scaffolds, which are found show promising anticancer activity. More importantly, theoretical calculations pathways activation mode offer in-depth understanding class indolylmethanols. This work not only settles challenges realizing indolyldimethanols but also provides a powerful strategy for rings.

Язык: Английский

Процитировано

54

Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols DOI Open Access
Haiqing Wang, Shuang Yang, Yu‐Chen Zhang

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(3), С. 974 - 974

Опубликована: Янв. 1, 2023

a 江苏师范大学化学与材料科学学院 江苏徐州 221116

Процитировано

28

Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds DOI

Ziqi Zhu,

Tian‐Zhen Li,

Sijia Liu

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(19), С. 5573 - 5604

Опубликована: Янв. 1, 2024

This review has summarized the development of organocatalytic asymmetric [3 + 3] cycloadditions and given insights into remaining challenges to promote future this field.

Язык: Английский

Процитировано

18

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

Jia-Bo Huang,

Dahua Wang

и другие.

Precision Chemistry, Год журнала: 2024, Номер 2(5), С. 208 - 220

Опубликована: Апрель 23, 2024

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

Язык: Английский

Процитировано

17

Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis DOI
Yuheng Wang, Pan Hu, Xirui Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1314 - 1321

Опубликована: Янв. 1, 2024

A new class of chiral bipyridine-2NO ligands, which incorporate the advantages both bipyridine skeleton and pyrroloimidazolone-based N -oxide moiety, was developed.

Язык: Английский

Процитировано

9

Chiral Phenol‐2NO Ligand Cooperation with Achiral Organic Base in the Zn(II)‐Catalyzed Asymmetric Alkylation Reaction of Indoles DOI

Ke‐Lan Xu,

Yuheng Wang, Xirui Wang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(13), С. 1474 - 1480

Опубликована: Март 1, 2024

Comprehensive Summary The privileged C 2 ‐symmetric rigid phenol‐type ligand is more attractive but challenging in asymmetric catalysis. Herein, we designed and synthesized a class of rigid‐featured chiral tridentate Phenol‐2NO ligands, that incorporate the advantages both phenol skeleton pyrroloimidazolone‐based N ‐oxide moiety, from readily available L ‐prolinamides operationally simple two steps up to 44% overall yield. More importantly, using an achiral quinoline derivative as additive, newly developed could serve anioic upon deprotonative activation coordinate Zn(II) form highly enantioselective catalyst for Michael‐type Friedel‐Crafts alkylation reaction indoles with 2,3‐dioxopyrrolidines. Excellent yields (up 90%) high enantioselectivities 99% ee) are obtained wide range substrates under mild conditions. Experiments DFT calculations revealed mechanism origins enantioselectivity. This also represented first ligand/metal complex by organic base additive

Язык: Английский

Процитировано

6

Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides DOI Open Access
Shuang Yang,

Ningyi Wang,

Qingqing Hang

и другие.

Acta Chimica Sinica, Год журнала: 2023, Номер 81(7), С. 793 - 793

Опубликована: Янв. 1, 2023

o-Hydroxyphenyl substituted p-quinone methides (p-QMs) belong to a class of p-QMs with unique advantages.They not only maintain the high reactivity p-QMs, but also have more reactive and activation sites owing introduction hydroxyl group.Therefore, o-hydroxyphenyl wide applications in synthetic medicinal chemistry.The catalytic asymmetric 1,6-conjugate addition [4+n] cycloaddition developed very rapidly recent years, which become efficient strategies for synthesis chiral oxygen-containing heterocycles arylmethanes potential bioactivity.This review summarizes reactions involving points out remaining challenges this research area, will open new window design type their involved reactions.

Язык: Английский

Процитировано

13

Enantioselective synthesis of tryptanthrin derivatives enabled by an asymmetric aza-Friedel–Crafts reaction DOI
Yong You,

Guo-Ying Gan,

Si-Yang Duan

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(21), С. 5421 - 5427

Опубликована: Янв. 1, 2023

A class of ketimines was first prepared and used in an asymmetric aza-Friedel–Crafts reaction for the highly enantioselective synthesis tryptanthrin derivatives.

Язык: Английский

Процитировано

12

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

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(7), С. 2040 - 2046

Опубликована: Янв. 1, 2024

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

Язык: Английский

Процитировано

5