A synthetic route to 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyranoindoles via ring-opening/Pictet–Spengler reaction of aziridines and epoxides with indoles/aldehydes DOI
Imtiyaz Ahmad Wani, Gaurav Goswami, sahid sk

et al.

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 18(2), P. 272 - 287

Published: Dec. 4, 2019

A route to 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyrano[3,4-b]indoles in high yields stereoselectivity via SN2-type ring opening/Pictet–Spengler reaction of aziridines epoxides with indoles is described.

Language: Английский

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

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(5), P. 1314 - 1321

Published: Jan. 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.

Language: Английский

Citations

9
Regio- and diastereoselective dearomatizations ofN-alkyl activated azaarenes: the maximization of the reactive sites DOI Creative Commons

Hong-Jie Miao,

Lele Wang,

Huabin Han

et al.

Chemical Science, Journal Year: 2019, Volume and Issue: 11(5), P. 1418 - 1424

Published: Dec. 17, 2019

An unprecedented base-promoted multi-component one-pot dearomatization ofN-alkyl activated azaarenes was developed to construct complex and diverse bridged cyclic polycycles with multiple stereocenters in a highly regio- diastereoselective manner.

Language: Английский

Citations

72
Dearomative Periphery Modification of Quinolinium Salts to Assemble Ring-Encumbered Pyrrolidine–Tetrahydroquinoline Polycycles DOI

Lijie Gu,

Huabin Han,

Zhanwei Bu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(10), P. 2008 - 2013

Published: March 10, 2022

We report an unexpected dearomative periphery modification strategy for transforming quinolinium salts into structurally crowded pyrrolidine–tetrahydroquinoline polycyclic systems with complete regio- and diastereoselectivity. Importantly, the reaction pathway was regulated by simply tuning substituents, achieving substituent-directed divergent synthesis. The notable features of this transformation include readily available starting materials, green conditions, a simple workup procedure, high bond- ring-forming efficiency, diverse

Language: Английский

Citations

29
Py-2NO ligand enabled Ni(ii)-catalyzed asymmetric Michael addition reaction of indoles with β,γ-unsaturated α-keto esters DOI

Zi‐Yue Chen,

Xirui Wang,

Ke‐Lan Xu

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(4), P. 1688 - 1695

Published: Jan. 1, 2024

This work diversified the Py-2NO ligand library recently developed by our group and further expanded application of chiral ligands in asymmetric catalysis.

Language: Английский

Citations

6
Regioselective and Diastereoselective Dearomative Multifunctionalization of In-Situ-Activated Azaarenes: An Access to Bridged Azaheterocycles DOI

Xuguan Bai,

Hong-Jie Miao,

Yang Zhao

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(13), P. 5068 - 5073

Published: May 27, 2020

Reported herein is an unprecedented multicomponent one-pot dearomative multifunctionalization of commercially available azaarenes through in situ activation strategy, which not only achieved the first full exploitation reactive sites azaarenes, but also accomplished efficient synthesis bridged hydrogenated pyridines and (iso)quinolines a highly regioselective diastereoselective manner. In addition, we could successfully realize step-controlled trifunctionalization bifunctionalization quinolines.

Language: Английский

Citations

42
Skeletal remodeling of chalcone-based pyridinium salts to access isoindoline polycycles and their bridged derivatives DOI Creative Commons
Lele Wang,

Huabin Han,

Lijie Gu

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(46), P. 15389 - 15398

Published: Jan. 1, 2021

A novel skeletal remodeling strategy to transform chalcone-based pyridinium salts into structurally intriguing polycyclic isoindolines was achieved through a dearomative ring-opening/ring-closing sequence.

Language: Английский

Citations

38
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

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(13), P. 1474 - 1480

Published: March 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

Language: Английский

Citations

5
An unexpected cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates to construct 2,3-dihydrobenzofuran spirooxindoles DOI
Kuan Zhang,

Huabin Han,

Lele Wang

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(91), P. 13681 - 13684

Published: Jan. 1, 2019

An unexpected Michael addition-inspired ring-opening/closure cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates was developed.

Language: Английский

Citations

37
Chalcone-Based Pyridinium Salts and Their Diastereoselective Dearomatization To Access Bibridged Benzoazepines DOI
Lele Wang,

Huabin Han,

Zhaohui Cui

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(3), P. 873 - 878

Published: Jan. 9, 2020

New chalcone-based pyridinium salts have been successfully exploited, which could smoothly participate in the highly diastereoselective dearomatization with binucleophilic enaminones by taking advantage of their multiple reactive sites to construct bibridged benzoazepines up 89% yields. The key success was skillful and unprecedented C-3 functionalization new salts. This work not only provides a kind novel salt synthon but also achieves first complex challenging high synthetic efficiency.

Language: Английский

Citations

37
Assembly of functionalized π-extended indolizine polycycles through dearomative [3+2] cycloaddition/oxidative decarbonylation DOI

Shaojing Jin,

Lele Wang,

Huabin Han

et al.

Chemical Communications, Journal Year: 2020, Volume and Issue: 57(3), P. 359 - 362

Published: Dec. 8, 2020

An unexpected construction of functionalized π-extended indolizine polycycles through a one-pot two-step process comprising the base-promoted dearomative [3+2] cycloaddition and DDQ-mediated oxidative decarbonylation was developed.

Language: Английский

Citations

35