Work

One-Pot Synthesis of Chiral Allenes Mediated by Decahydroquinoxaline Scaffolds

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide We report a direct and efficient one-pot strategy for the synthesis of highly enantioselective ( R )-allenes using 1-alkynes and aromatic aldehydes mediated by decahydroquinoxaline scaffolds. The reaction, promoted by ZnI 2 in toluene at 120 °C, proceeds smoothly under mild conditions, affording chiral allenes with good yields (57–85% for aliphatic alkynes and 25% for the aromatic alkyne) and excellent enantioselectivities (83–96%) within 4 h. This method offers a straightforward and practical approach for constructing valuable chiral allene frameworks that are potentially useful in organic synthesis and medicinal chemistry. The use of decahydroquinoxaline scaffolds enables effective chirality transfer, making this protocol a promising tool for stereoselective transformation.

Source: ACS Omega

DOI: 10.1021/acsomega.5c04812

Authors: Laxman Mahadev Alakonda, Mariappan Periasamy

Institutions: University of Wyoming, University of Hyderabad

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,935

Funders: Department of Science and Technology, Ministry of Science and Technology, India, Council of Scientific and Industrial Research, India, University Grants Commission, University of Hyderabad