One-Step Construction of Atropisomers Bearing 1,5-Central and Axial Chirality via Catalytic Diastereo- and Atroposelective Remote Desymmetrizing Alkynylation DOI
Shan Wang, Long Li, Ming Jiang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 18872 - 18883

Published: Dec. 11, 2024

Catalytic asymmetric construction of atropisomers with multiple stereogenic elements has recently become an emerging area. However, general methods that produced bearing remote 1,5-axial and central chirality efficiently stereoselectively are scarce yet highly challenging. We herein report a catalytic diastereo- atroposelective desymmetrizing alkynylation axially prochiral dialkynes ortho-quinone methides (o-QMs), furnishing 1,5-remote centrally elements. The control axis far from the reaction site could be simultaneously achieved during stereoselective C(sp3)–C(sp) bond-forming process to generate center. In addition, kinetic resolution racemic alkynes via o-QMs been developed, further enriching structural diversity 1,5-central axial chirality. present method expands chemical space atropisomeric molecules chiral by facile downstream diversification C–C triple bonds. Finally, can also applied for motifs 1,9- 1,10-stereogenic centers.

Language: Английский

Copper-catalyzed enantioselective desymmetrizing C(sp2)–H functionalization of azide-ynamides via α-imino copper carbenes DOI

En‐He Huang,

Li‐Gao Liu,

Yin You-wei

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(9), P. 2982 - 2988

Published: July 3, 2024

Language: Английский

Citations

4
Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement DOI

Ji‐Jia Zhou,

Li‐Gao Liu, Zhentao Zhang

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110870 - 110870

Published: Jan. 1, 2025

Language: Английский

Citations

0
Chiral Phosphoric Acid-Catalyzed Kinetic Resolution of Tertiary Alcohol-Tethered Ynamides via Controllable Hydroalkoxylation DOI

Da-Qiu Cui,

Gan-Lu Qian,

Hongxing Zheng

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 2424 - 2433

Published: Jan. 27, 2025

Language: Английский

Citations

0
Organocatalytic Atroposelective Reactions of Alkynes DOI
Bo Zhou, Zhixin Zhang,

Tian-Qi Hu

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(15), P. 2316 - 2328

Published: Jan. 9, 2024

Abstract The atroposelective transformation of alkynes is an efficient protocol for the assembly axially chiral compounds. Benefitting from rapid development organocatalysts, organocatalytic reactions have been extensively studied over past decades. An array catalysts, including Brønsted acid secondary amine N-heterocyclic carbene (NHC) thiourea catalysts and N-squaramide are employed in enantioselective different alkynes. This short review summarizes recent advances on according to type alkyne substrate. reaction mechanisms, modes enantiocontrol, product diversity applications highlighted. 1 Introduction 2 Electron-Rich Aryl Alkynes 3 Electron-Deficient 4 Other Types 5 Conclusion Outlook

Language: Английский

Citations

2
Gold-catalyzed intermolecular amination of allyl azides with ynamides: efficient construction of 3-azabicyclo[3.1.0] scaffold DOI

Chong‐Yang Shi,

Jianxing Gong,

Zhen Li

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(2), P. 109895 - 109895

Published: April 17, 2024

Language: Английский

Citations

2
Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles DOI

Jiasheng Wang,

Ze‐Shu Wang, Wei‐Min He

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(6), P. 1786 - 1786

Published: Jan. 1, 2024

Language: Английский

Citations

2
Brønsted-Acid-Catalyzed Enantioselective Desymmetrization of 1,3-Diols: Access to Chiral β-Amino Alcohol Derivatives DOI

Da-Qiu Cui,

Yuqi Wang, Bo Zhou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9130 - 9135

Published: Dec. 19, 2023

Herein, we describe a Brønsted-acid-catalyzed enantioselective desymmetrization of 1,3-diols with alkynes through hydroalkoxylation/hydrolysis process. The reaction leads to the atom-economical synthesis valuable chiral β-amino alcohols under mild conditions. Further synthetic transformations based on alcohol moiety provide divergent approaches toward N-containing heterocycles.

Language: Английский

Citations

2
One-Step Construction of Atropisomers Bearing 1,5-Central and Axial Chirality via Catalytic Diastereo- and Atroposelective Remote Desymmetrizing Alkynylation DOI
Shan Wang, Long Li, Ming Jiang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 18872 - 18883

Published: Dec. 11, 2024

Catalytic asymmetric construction of atropisomers with multiple stereogenic elements has recently become an emerging area. However, general methods that produced bearing remote 1,5-axial and central chirality efficiently stereoselectively are scarce yet highly challenging. We herein report a catalytic diastereo- atroposelective desymmetrizing alkynylation axially prochiral dialkynes ortho-quinone methides (o-QMs), furnishing 1,5-remote centrally elements. The control axis far from the reaction site could be simultaneously achieved during stereoselective C(sp3)–C(sp) bond-forming process to generate center. In addition, kinetic resolution racemic alkynes via o-QMs been developed, further enriching structural diversity 1,5-central axial chirality. present method expands chemical space atropisomeric molecules chiral by facile downstream diversification C–C triple bonds. Finally, can also applied for motifs 1,9- 1,10-stereogenic centers.

Language: Английский

Citations

0