Enantioselective “clip-cycle” synthesis of di-, tri- and spiro-substituted tetrahydropyrans

Alomari, Khadra; Sai Pavan Chakravarthy, N.; Duchadeau, Bastien; Ermanis, Kristaps; Clarke, Paul A.

Abstract

ω-Unsaturated alcohols were “clipped” via alkene metathesis to a thioester activating group, which was followed by a chiral phosphoric acid catalyzed intramolecular oxa-Michael cyclization to yield tetrahydropyrans and spiro-tetrahydropyrans with excellent enantioselectivity. The mechanism and origin of the enantioselectivity was probed by DFT calculations and kinetic isotope studies, where there was excellent correlation between the computational and synthetic investigations.

Citation

Alomari, K., Sai Pavan Chakravarthy, N., Duchadeau, B., Ermanis, K., & Clarke, P. A. (2022). Enantioselective “clip-cycle” synthesis of di-, tri- and spiro-substituted tetrahydropyrans. Organic and Biomolecular Chemistry, 20(6), 1181-1185. https://doi.org/10.1039/d2ob00023g

• Journal Article Type: Article
• Acceptance Date: Jan 13, 2022
• Online Publication Date: Jan 13, 2022
• Publication Date: Feb 14, 2022
• Deposit Date: Feb 1, 2022
• Publicly Available Date: Jan 14, 2023
• Journal: Organic & Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 20
• Issue: 6
• Pages: 1181-1185
• DOI: https://doi.org/10.1039/d2ob00023g
• Keywords: Organic Chemistry; Physical and Theoretical Chemistry; Biochemistry
• Public URL: https://nottingham-repository.worktribe.com/output/7371579
• Publisher URL: https://pubs.rsc.org/en/content/articlelanding/2022/OB/D2OB00023G