Chiral Brønsted Acid Catalyzed Cascade Alcohol Deprotection and Enantioselective Cyclization.

ACS Omega

Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, 320 College Avenue, Greensboro, North Carolina 27412, United States.

Published: January 2024

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10795110PMC
http://dx.doi.org/10.1021/acsomega.3c08869DOI Listing

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