Intermolecular Enamine Mizoroki-Heck Reactions on a Bio-Derived Scaffold.
J Org Chem
; 89(2): 1315-1319, 2024 Jan 19.
Article
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| MEDLINE
| ID: mdl-38190610
ABSTRACT
The intramolecular enamine-Mizoroki-Heck reaction allows for the construction of nitrogen-containing heterocycles, although the related intermolecular version is less known. The reactions of enamines derived from Cyrene were investigated under Mizoroki-Heck conditions. An optimization study was used to identify that 1.5 mol % Pd(dba)2 with PCy3 in xylene at reflux temperature gave the highest yield with electron-rich aryl iodides. Arylation occurred predominantly at the C-N center of the enamine, while the diastereoselectivity was dependent on the nitrogen substitution in the enamine.
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MEDLINE
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2024
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Article