Enantioselective “Clip-Cycle” Synthesis of Di-, Tri- and Spiro- Substituted Tetrahydropyrans

Paul Andrew Clarke, Khadra Alomari, Sai Pavan Chakravarthy, Bastien Duchadeau, Kristaps Ermanis

Research output: Contribution to journalArticlepeer-review

Abstract

-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
Original languageEnglish
Pages (from-to)1181-1185
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume20
Issue number6
DOIs
Publication statusPublished - 13 Jan 2022

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