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Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans.

O'Brien, M; Tizzard, GJ; Coles, SJ; Cooper, DA; Robbins, E

Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans. Thumbnail


Authors

GJ Tizzard

SJ Coles

DA Cooper

E Robbins



Abstract

Combining the desymmetrization of a prochiral bis-hydroxymethyl group with the epimerization of a chiral furanyl ether in a single transformation, high levels of double diastereoselectivity have been achieved in a synthesis of 2,4,5-trisubstituted tetrahydropyrans, which proceeds under thermodynamic control.

Acceptance Date Nov 27, 2016
Publication Date Feb 28, 2017
Publicly Available Date Mar 28, 2024
Journal Journal Of Organic Chemistry
Print ISSN 0022-3263
Publisher American Chemical Society
Pages 3441-3455
DOI https://doi.org/10.1021/acs.joc.6b02831
Publisher URL http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02831