Five-membered ring systems with O and N atoms DOI
Franca M. Cordero, Donatella Giomi, Fabrizio Machetti

et al.

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 351 - 382

Published: Jan. 1, 2023

Language: Английский

Recent Progress in Chiral Quaternary Ammonium Salt-Promoted Asymmetric Nucleophilic Additions DOI
Xiaoqun Yang,

Youlin Deng,

Dan Ling

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1973 - 2001

Published: Jan. 20, 2025

Chiral quaternary ammonium ion-pair organocatalysis has been widely used in the facile synthesis of chiral molecules with challenging stereocenters. Especially, numerous asymmetric nucleophilic addition reactions have facilitated this strategy. This review systematically summarizes additions promoted by salts past decade. The content is organized according to types electrophiles involved these catalytic transformations. Our own perspectives on future development within highly active research field are also provided.

Language: Английский

Citations

0
Towards an asymmetric β-selective addition of azlactones to allenoates DOI Creative Commons
Behzad Nasiri,

Ghaffar Pasdar,

Paul Zebrowski

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1504 - 1509

Published: July 4, 2024

We herein report the asymmetric organocatalytic addition of azlactones to allenoates. Upon using chiral quaternary ammonium salt catalysts, i.e., Maruoka’s binaphthyl-based spirocyclic salts, various allenoates proceeds in a β-selective manner with moderate levels enantioselectivities (up 83:17 er). Furthermore, obtained products can be successfully engaged nucleophilic ring opening reactions, thus giving highly functionalized α-amino acid derivatives.

Language: Английский

Citations

2
Chiral Quaternary Ammonium Salt‐Catalyzed Enantioselective Addition Reactions of Hydantoins DOI Creative Commons

Katharina Röser,

Lucas Prameshuber,

Sajid Jahangir

et al.

Helvetica Chimica Acta, Journal Year: 2023, Volume and Issue: 107(3)

Published: Dec. 29, 2023

Abstract We herein report a protocol for the asymmetric 1,4‐addition of hydantoins to various Michael acceptors by utilizing Cinchona alkaloid‐based chiral quaternary ammonium salt catalysts. Various products were obtained with moderate good enantioselectivities and accompanying computational investigations helped identify key interactions responsible observed selectivity. DFT calculations along non‐covalent interaction plots reveal presence numerous stabilizing non‐classical hydrogen bonding other between hydantoin molecule in C−C bond forming transition states leading formation products. In addition, first proof‐of‐concept an analogous a‐sulfanylation reaction, albeit poor selectivity, is reported as well.

Language: Английский

Citations

4
DBU-catalyzed selective β-addition of α-fluoro nitroalkanes to allenoates DOI

Li-Wen Ning,

Yi‐Hu Jin,

R. Wang

et al.

Journal of Fluorine Chemistry, Journal Year: 2024, Volume and Issue: 274, P. 110255 - 110255

Published: Jan. 21, 2024

Language: Английский

Citations

1
Five-membered ring systems with O and N atoms DOI
Franca M. Cordero, Donatella Giomi, Fabrizio Machetti

et al.

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 351 - 382

Published: Jan. 1, 2023

Language: Английский

Citations

0