Work

Chiral Brønsted Acid Catalyzed Cascade Alcohol Deprotection and Enantioselective Cyclization

Year: 2023

Type: article

Abstract: The protection-deprotection sequence is vital to organic synthesis. Here, we describe a novel catalytic cascade where a chiral Brønsted acid selectively removes ether protecting groups and catalyzes intramolecular cyclization in one pot. We tested three model substrates from our previous work and investigated the rate of deprotection through gas chromatography (GC) studies. This work builds on our stereoselective synthesis of lactones by streamlining our synthesis. It also opens the door for additional investigations into other catalytic cascade reactions using chiral Brønsted acid catalysts.

Source: ACS Omega

DOI: 10.1021/acsomega.3c08869

Authors: Joshua A. Frost, Sarah M. Korb, Fiona E. Green, Kala C. Youngblood, Kimberly S. Petersen

Institution: University of North Carolina at Greensboro

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,685

Funders: U.S. Department of Health and Human Services, University of North Carolina at Greensboro, National Institute of General Medical Sciences, National Center for Complementary and Integrative Health