Diastereoselective Synthesis of 2,3,4-Trisubstituted Tetrahydrofurans via Thermally Reactive 1,5-Diene-tert-butyl Carbonates

We report that 3,3-dicyano-1,5-dienes bearing tert-butyl carbonates can be thermally converted to 2,3,4-trisubstituted tetrahydrofurans. The transformation relies on two thermally reactive functional groups, a 1,5-diene and a tert-butyl carbonate, that react cooperatively to yield the furan scaffold...

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Bibliographic Details
Published in:Organic letters 2020-02, Vol.22 (3), p.842-847
Main Authors: Emmetiere, Fabien, Grenning, Alexander J
Format: Article
Language:English
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Summary:We report that 3,3-dicyano-1,5-dienes bearing tert-butyl carbonates can be thermally converted to 2,3,4-trisubstituted tetrahydrofurans. The transformation relies on two thermally reactive functional groups, a 1,5-diene and a tert-butyl carbonate, that react cooperatively to yield the furan scaffolds by thermal Cope rearrangement, Boc deprotection, and oxy-Michael addition. Described herein is background related to the discovery, optimization, and scope of the key transformation and representative functional group interconversion chemistry for the tetrahydrofuran scaffolds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04306