Journal
ORGANIC LETTERS
Volume 10, Issue 6, Pages 1139-1142Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol8000409
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- NIGMS NIH HHS [P50-GM067082] Funding Source: Medline
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In this manuscript we report that intramolecular Friedel-Crafts alkylation reactions of aryl-substituted alpha-alkoxy acylimines proceed in the presence of mild Lewis acids to afford bicyclic beta-alkoxy amides. The intermediate acylimines are prepared through cyanohydrin ether hydrozirconation and acylation of the resulting metalloimine, providing an operationally facile one pot protocol. A two-step variant of the procedure has also been developed to effect cyclizations from acylimines that undergo competitive tautomerization.
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