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Convergent Synthesis of Trisubstituted Tetrahydrofurans via Bis-Thermally Reactive 1,5-Diene-Tert-Butyl Carbonates.

preprint
submitted on 31.10.2019 and posted on 06.11.2019 by Alex Grenning, Fabien Emmetiere

Cascade reactions (also known as domino- or tandem reactions) are an efficient strategy for generating molecular complexity. We report that synergizing the thermal reactivity of 3,3-dicyano-1,5-dienes and tert-butyl carbonates result in stereospecific 2,3,4-trisubstituted tetrahydrofuran synthesis. While substituted tetrahydrofurans can be challenging to synthesize, this discovery converts readily available 1,5-dienes derived from aldehydes, malononitrile, and cis-buten-1,4-diol into complex tetrahydrofurans via a process involving thermal Cope rearrangement, Boc-deprotection, and oxy-Michael addition. Described herein includes background related to the discovery, optimization and scope, and representative functional group interconversion chemistry for the scaffolds.

Funding

This material is based upon work supported by the National Science Foundation under Grant No. 1844443

History

Email Address of Submitting Author

grenning@ufl.edu

Institution

University of Florida

Country

United States of America

ORCID For Submitting Author

0000-0002-8182-9464

Declaration of Conflict of Interest

No Conflict of Interest

Version Notes

This is Version 1 of this Manuscript

Exports