1,2,4-Trifunctionalized Cyclohexane Synthesis via a Diastereoselective Reductive Cope Rearrangement and Functional Group Interconversion Strategy

Michael D Mannchen; Ion Ghiviriga; Khalil A Abboud; Alexander J Grenning

doi:10.1021/acs.orglett.1c03310

1,2,4-Trifunctionalized Cyclohexane Synthesis via a Diastereoselective Reductive Cope Rearrangement and Functional Group Interconversion Strategy

Org Lett. 2021 Nov 19;23(22):8804-8809. doi: 10.1021/acs.orglett.1c03310. Epub 2021 Nov 1.

Authors

Michael D Mannchen¹, Ion Ghiviriga², Khalil A Abboud³, Alexander J Grenning¹

Affiliations

¹ Department of Chemistry, University of Florida, Gainesville, Florida 32603, United States.
² Center for NMR Spectroscopy, Department of Chemistry, University of Florida, Gainesville, Florida 32603, United States.
³ Center for X-ray Crystallography, Department of Chemistry, University of Florida, Gainesville, Florida 32603, United States.

PMID: 34719933
DOI: 10.1021/acs.orglett.1c03310

Abstract

Polyfunctionalized cyclohexanes are privileged scaffolds in drug discovery. Reported herein is a method for synthesizing 1,2,4-trifunctionalized cyclohexanes via diastereoselective reductive Cope rearrangement. The scaffolds obtained can be derivatized by orthogonal functional group interconversion to cyclohexanes bearing a 1-amide, 2-branched arylallyl, and variable 4-functional group.