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

Fabien Emmetiere, Alexander J. Grenning

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)842-847
Number of pages6
JournalOrganic Letters
Volume22
Issue number3
DOIs
StatePublished - Feb 7 2020
Externally publishedYes

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

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