Access to Indole-Annulated Medium-Sized Lactams through Protonation/Deuteration-Induced Ring-Opening of Spiroindolines DOI

Jianhui Qiao,

Huili Liu, Shaozhong Wang

et al.

ACS Omega, Journal Year: 2021, Volume and Issue: 6(38), P. 25049 - 25061

Published: Sept. 14, 2021

A protocol has been developed to access indole-annulated eight- and nine-membered lactams through protonation-induced ring-opening of spiroindolines, which are dearomative Heck products tetrahydro-β-carbolines or hexahydroazepino[3,4-b]indoles. Brønsted acids nucleophiles were explored compared in the transformation. combination deuterated hydrochloride methanol enables deuterative spiroindolines afford medium-sized lactam diastereoisomers with a deuterium content ratio around 1:1.

Language: Английский

Modular enantioselective access to β-amino amides by Brønsted acid-catalysed multicomponent reactions DOI Open Access
Jun Wei, Jian Zhang, Jun Kee Cheng

et al.

Nature Chemistry, Journal Year: 2023, Volume and Issue: 15(5), P. 647 - 657

Published: April 13, 2023

Language: Английский

Citations

24
Chiral Brønsted acid-catalyzed asymmetric intermolecular [4 + 2] annulation of ynamides with para-quinone methides DOI

Hang‐Hao Li,

Ya-Nan Meng,

Can‐Ming Chen

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(5), P. 1467 - 1473

Published: April 12, 2023

Language: Английский

Citations

19
Steric-switched defluorofunctionalization selectivity: controlled synthesis of monofluoroalkene-masked medium-sized heterocyclic lactams and lactones DOI
Hao Zeng, Hengyuan Li, Huanfeng Jiang

et al.

Science China Chemistry, Journal Year: 2021, Volume and Issue: 65(3), P. 554 - 562

Published: Dec. 6, 2021

Language: Английский

Citations

36
Construction of enantioenriched eight-membered lactones via Pd-catalyzed asymmetric (6+2) dipolar annulation DOI

Baocheng Wang,

Wei Yi,

Feng-Ya Xiong

et al.

Science China Chemistry, Journal Year: 2022, Volume and Issue: 65(12), P. 2437 - 2443

Published: Nov. 3, 2022

Language: Английский

Citations

18
Metal-free dearomatization reactions of naphthol-ynamides for the divergent and enantioselective synthesis of azaspirocycles DOI

Hang‐Hao Li,

Yiping Zhang,

Tong‐Yi Zhai

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(14), P. 3709 - 3717

Published: Jan. 1, 2022

An efficient Brønsted acid (BA) catalyzed intramolecular dearomatization cyclization of naphthol-ynamides has been developed, enabling the practical and divergent synthesis two azaspirocycles in high yields.

Language: Английский

Citations

15
Transition metal catalysed cascade C–C and C–O bond forming events of alkynes DOI

Padmanava Barik,

Subhra Sriharsa Behera,

Laxmi Kanta Nayak

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(25), P. 5052 - 5086

Published: Jan. 1, 2024

1,2/1,1-Difunctionalization of alkynes (cascade C–C and C–O bond formations) serves as one the reliable methods for synthesis numerous chemical architectures.

Language: Английский

Citations

3
A copper-catalyzed B–H bond insertion reaction of azide–ynamide with borane adductsviaα-imino copper carbenes DOI

Chen-Yong Weng,

Guang‐Yu Zhu,

Bo‐Han Zhu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(10), P. 2773 - 2778

Published: Jan. 1, 2022

A new copper-catalyzed B–H bond insertion into α-imino copper carbenes generated from azide–ynamide cyclization has been developed, leading to a facile and practical synthesis of series α-boryl amidines.

Language: Английский

Citations

13
Copper-catalyzed formal [4 + 1] annulation ofN-propargyl ynamides with diketones DOI

Hao-Jin Xu,

Cui‐Ting Li,

Can‐Ming Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(1), P. 203 - 208

Published: Nov. 24, 2022

An efficient copper-catalyzed formal [4 + 1] annulation of N -propargyl ynamides with diketones has been developed, allowing practical and atom-economic synthesis valuable pyrrole-substituted dioxoles in generally moderate to excellent yields.

Language: Английский

Citations

10
Copper-Catalyzed Si–H Bond Insertion Reaction of N-Propargyl Ynamides with Hydrosilanes DOI

En‐He Huang,

Yingqi Zhang,

Da-Qiu Cui

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 24(1), P. 196 - 201

Published: Dec. 21, 2021

Transition-metal-catalyzed Si-H bond insertion reactions are generally limited to stabilized diazo compounds. An efficient copper-catalyzed reaction of N-propargyl ynamides with hydrosilanes is described, allowing practical and atom-economic construction valuable organosilanes in moderate excellent yields under mild conditions. Notably, this constitutes a new method involving vinyl cations as key intermediates.

Language: Английский

Citations

12
Efficient synthesis of tetracyclic γ-lactamsviagold-catalyzed oxidative cyclization of alkenyl diynes DOI

Chong‐Yang Shi,

Ji‐Jia Zhou,

Pan Hong

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(9), P. 2557 - 2562

Published: Jan. 1, 2022

An efficient gold-catalyzed cascade cyclization of alkenyl diynes involving alkyne oxidation, carbene-alkyne metathesis and cyclopropanation has been developed, affording various tetracyclic γ-lactams in moderate to good yields.

Language: Английский

Citations

9