Cinchona Organocatalyzed Enantioselective Amination for Quaternized Serines as Tertiary Amides DOI Creative Commons
Phathutshedzo Masithi,

Ashlyn D. Bhana,

Gerhard A. Venter

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(42), P. 9162 - 9167

Published: Oct. 16, 2024

Herein, we describe a Cinchona-aminocatalyzed enantioselective α-hydrazination of an α-formyl amide for the production protected quaternized serines as tertiary amides with ee's generally >98% and ≤99% yields. The proposed TS model supported by density functional theory calculations involves quinuclidinium ion Brønsted acid-assisted delivery DtBAD, which occurs from Re face H-bonded enaminone when using 9S-cinchonamine catalyst, resulting in hydrazide R-configuration determined X-ray analysis.

Language: Английский

Synergistic Pd/Ag-Catalyzed Domino Reaction: Access to Tetrahydropyrano[4,3-c]pyran and Hexahydrofuro[2,3-b]pyran DOI

Dipak B. Deokar,

Roumi Patra, Y. Bhargav Kumar

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

We report the Pd-catalyzed and Ag-mediated temperature-dependent divergent synthesis of tetrahydropyrano[4,3-c]pyran hexahydrofuro[2,3-b]pyran derivatives from a single substrate, alkynols. The reaction involves homocoupling alkynols to form two C–O bonds one C–C bond, resulting in cores at high temperature (110 °C). Exposing tetrahydropyrano[4,3-c]pyrans 200 W tungsten filament bulb yields tetrahydrofuro[2,3-b]pyrans. At lower temperatures (30–60 °C), produce hexahydrofuro[2,3-b]pyrans. density functional theory study explains selectivity.

Language: Английский

Citations

1
Editorial: Six-membered heterocycles: their synthesis and bio applications DOI Creative Commons
Pezhman Shiri,

Atefeh Roosta,

Sorour Ramezanpour

et al.

Frontiers in Chemistry, Journal Year: 2023, Volume and Issue: 11

Published: June 8, 2023

EDITORIAL article Front. Chem., 08 June 2023Sec. Organic Chemistry Volume 11 - 2023 | https://doi.org/10.3389/fchem.2023.1229825

Language: Английский

Citations

5
Synthesis and biological evaluation of some new heterocyclic derivatives from substituted thiopyrimidine DOI Creative Commons

Hadil. S. AZİZ,

Intisar Qahtan Mahmood Al-araj,

Linda Abdul-Raheem

et al.

Journal of the Serbian Chemical Society, Journal Year: 2024, Volume and Issue: 00, P. 67 - 67

Published: Jan. 1, 2024

This study aimed at creation of a few new heterocyclic compounds that include sulfur and nitrogen atoms. Also, some chalcones, thiazolidine, Schiff base derivatives have been prepared. The spectroscopic data (IR,1H 13C-NMR) verified the structure produced molecules. Interesting findings were obtained when several synthetic substances physiologically tested against range pathogenic Gram-positive Gram-negative bacteria.

Language: Английский

Citations

0
Cinchona Organocatalyzed Enantioselective Amination for Quaternized Serines as Tertiary Amides DOI Creative Commons
Phathutshedzo Masithi,

Ashlyn D. Bhana,

Gerhard A. Venter

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(42), P. 9162 - 9167

Published: Oct. 16, 2024

Herein, we describe a Cinchona-aminocatalyzed enantioselective α-hydrazination of an α-formyl amide for the production protected quaternized serines as tertiary amides with ee's generally >98% and ≤99% yields. The proposed TS model supported by density functional theory calculations involves quinuclidinium ion Brønsted acid-assisted delivery DtBAD, which occurs from Re face H-bonded enaminone when using 9S-cinchonamine catalyst, resulting in hydrazide R-configuration determined X-ray analysis.

Language: Английский

Citations

0