Organocatalytic Asymmetric Construction of Spirooxazines via Chemoselective Cascade Addition of N-Substituted Hydroxylamine with Keto-bis-enone DOI

Prasenjit Gayen,

Prasanta Ghorai

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6185 - 6190

Published: July 18, 2024

Spirooxazines represent a privileged heterocyclic scaffold having pronounced biological importance. Herein, we introduce chiral bifunctional squaramide catalyzed highly chemoselective cascade reaction involving aza-Michael/1,2-addition/oxa-Michael addition of

Language: Английский

What’s new in flow biocatalysis? A snapshot of 2020–2022 DOI Creative Commons
Michele Crotti, Marina Simona Robescu, Juan M. Bolívar

et al.

Frontiers in Catalysis, Journal Year: 2023, Volume and Issue: 3

Published: April 21, 2023

Flow biocatalysis is a key enabling technology that increasingly being applied to wide array of reactions with the aim achieving process intensification, better control biotransformations, and minimization waste stream. In this mini-review, selected applications flow preparation food ingredients, APIs fat- oil-derived commodity chemicals, covering period 2020-2022, are described.

Language: Английский

Citations

13

Photoredox-Mediated Radical Addition/Cyclization To Construct Benzannulated 6,5-Spiroketal Glycosides DOI
Chen Li, Shouyun Yu

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

Published: Jan. 30, 2025

We herein present a green and mild photoredox strategy for constructing framework of benzannulated 6,5-spiroketal glycosides. This method employs various O-arylacetylene glycosides aryl ketone acids as the starting materials, facilitating rapid straightforward synthesis with up to 92% yields under catalytic conditions. efficient approach has potential significantly enhance molecular library carbohydrate-based pharmaceuticals.

Language: Английский

Citations

0

Photocatalytic Synthesis and Functionalization of Sulfones, Sulfonamides and Sulfoximines DOI
José J. Garrido‐González, Katy Medrano‐Uribe, Cristian Rosso

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: July 22, 2024

Sulfur(VI)-based functional groups are popular scaffolds in a wide variety of research fields including synthetic and medicinal chemistry, as well chemical biology. The growing interest sulfur(VI)-containing molecules has motivated the scientific community to explore new methods synthesize modify them. Here, photocatalysis plays key role granting access types reactivity under mild reaction conditions. In this Perspective, we present selection works reported last six years focused on photocatalytic assembly sulfones, sulfonamides, sulfoximines. We addressed intermediates for each transformation, while discussing limitations strength points protocols. Future directions field finally presented.

Language: Английский

Citations

3

Rapid and Safe Continuous‐Flow Simmons‐Smith Cyclopropanation using a Zn/Cu Couple Column DOI Creative Commons
José Luis Nova‐Fernández,

Gustavo Pascual‐Coca,

Silvia Cabrera

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(4), P. 710 - 716

Published: Sept. 14, 2023

Abstract Flow chemistry has recently opened new windows thanks to the safer use of hazardous and sensitive reagents. Furthermore, flow procedures usually outperform their batch counterparts due improved mass heat transfer, offering a good opportunity for industrial application. Herein, rapid Simmons‐Smith cyclopropanation process is presented. Taking advantage in situ production zinc carbenoid species, several olefins bearing aromatic rings different electronic nature, aliphatic chains or heterocycles were smoothly cyclopropanated with residence time just 15 minutes. In addition, applicability protocol assured successful 12‐mmol scale experiment, which represents 3.59 grams per hour selected example, satisfactory synthesis pharmaceutical drugs.

Language: Английский

Citations

9

Carbene-controlled regioselectivity in photochemical cascades DOI Creative Commons
Mara Di Filippo, Marcus Baumann

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(14), P. 2930 - 2934

Published: Jan. 1, 2023

The discovery of an efficient regioselective photochemical flow process towards complex polycyclic scaffolds is reported.

Language: Английский

Citations

5

Modular Synthesis of Polar Spirocyclic Scaffolds Enabled by Radical Chemistry DOI
Khadijah Anwar, Francisco José Aguilar Troyano, Ayham H. Abazid

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(18), P. 3216 - 3221

Published: May 2, 2023

Herein, we report a highly modular strategy to access spirocyclic scaffolds from abundant starting materials, i.e., cyclic ketones and α-amino or oxamic acids. The sequence proceeds through straightforward Knoevenagel condensation, followed by domino Giese-type reaction/base-mediated cyclization process, deliver broad scope of polar in good excellent yields. products can be readily diversified, thus increasing the versatility our method gain rapid libraries potential druglike molecules.

Language: Английский

Citations

3

Organocatalytic Asymmetric Construction of Spirooxazines via Chemoselective Cascade Addition of N-Substituted Hydroxylamine with Keto-bis-enone DOI

Prasenjit Gayen,

Prasanta Ghorai

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6185 - 6190

Published: July 18, 2024

Spirooxazines represent a privileged heterocyclic scaffold having pronounced biological importance. Herein, we introduce chiral bifunctional squaramide catalyzed highly chemoselective cascade reaction involving aza-Michael/1,2-addition/oxa-Michael addition of

Language: Английский

Citations

0