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

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...

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Veröffentlicht in:Organic letters 2021-11, Vol.23 (22), p.8804-8809
Hauptverfasser: Mannchen, Michael D, Ghiviriga, Ion, Abboud, Khalil A, Grenning, Alexander J
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03310