Mechanisms and Origins of Regio- and Stereoselectivities in NHC-Catalyzed [3 + 3] Annulation of α-Bromoenals and 5-Aminoisoxazoles: A DFT Study DOI

Mingchao Zhang,

Zhiqiang Zhang, Yan Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10748 - 10759

Published: July 12, 2024

Density functional theory (DFT) calculations were conducted to explore the mechanisms and origins of regio- stereoselectivities underlying [3 + 3] annulation reaction between α-bromoenals 5-aminoisoxazoles with

Language: Английский

NHC‐Catalyzed Enantioselective Transformations Involving α‐Bromoenals DOI
Fatemeh Doraghi,

Mahmoud Ameli,

Shirin Ansariashlaghi

et al.

The Chemical Record, Journal Year: 2024, Volume and Issue: 24(5)

Published: April 8, 2024

Abstract α‐Haloenals, especially, α‐bromoenals considered as one of the important building blocks in organic synthesis. They can participate various (3+2)‐, (3+3)‐, (3+4)‐, and (2+4)‐annulation reactions with other molecules presence an NHC catalyst to produce enantioenriched carbo‐, heterocyclic compounds. Herein, we have described NHC‐catalyzed enantioselective transformations synthesis heterocycles, carbocycles, well acyclic

Language: Английский

Citations

4
Asymmetric electrophilic functionalization of amino-substituted heteroaromatic compounds: a convenient tool for the enantioselective synthesis of nitrogen heterocycles. DOI
Gonzalo Blay, Alicia Monleón, Marc Montesinos‐Magraner

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The catalytic asymmetric electrophilic functionalization of the less reactive N-heteroaromatic compounds has been reported using approach introduction an exocyclic amino substituent.

Language: Английский

Citations

2
Recent advances in the catalytic asymmetric construction of axially chiral azole-based frameworks DOI
Weiwei Luo, Yu Zhang,

Meijun Ming

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6819 - 6849

Published: Jan. 1, 2024

This review highlights recent advances in the atroposelective preparation of axially chiral azole derivatives, emphasizing mechanistic insights and synthetic applications development this class five-membered heterocyclic frameworks.

Language: Английский

Citations

2
Asymmetric synthesis of chiral pyrazolo[3,4-b]pyridin-6-ones under carbene catalysis DOI
Qianqian Wu,

Jinna Han,

Jie Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(34), P. 6898 - 6902

Published: Jan. 1, 2023

A structurally diverse set of chiral pyrazolo[3,4- b ]pyridin-6-ones was efficiently prepared in excellent yields with enantioselectivities via N-heterocyclic carbene-catalyzed oxidative [3 + 3] annulation enals pyrazol-5-amines.

Language: Английский

Citations

4
Enantioselective Synthesis of Axially Chiral Heterobiaryl N‐Cbz‐Protected Diamines via Organocatalytic Arylation of 5‐Aminoisoxazoles DOI
Qian Li, Yuanyuan Xu, Tao Wang

et al.

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

Published: June 8, 2024

Abstract An enantioselective arylation of isoxazoles with N‐Cbz‐protected azonaphthalenes is disclosed, affording a range axially chiral arylisoxazoles in good yields and excellent enantiocontrol by utilizing phosphoric acid. Cbz protecting group can be readily removed, resulting five‐six membered heterobiaryl amines bearing free amine maintaining enantiomeric purity.

Language: Английский

Citations

1
Mechanisms and Origins of Regio- and Stereoselectivities in NHC-Catalyzed [3 + 3] Annulation of α-Bromoenals and 5-Aminoisoxazoles: A DFT Study DOI

Mingchao Zhang,

Zhiqiang Zhang, Yan Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10748 - 10759

Published: July 12, 2024

Density functional theory (DFT) calculations were conducted to explore the mechanisms and origins of regio- stereoselectivities underlying [3 + 3] annulation reaction between α-bromoenals 5-aminoisoxazoles with

Language: Английский

Citations

0