One-pot synthesis of bicyclic beta-alkoxy amides from cyanohydrin ethers.
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.
Xiao
Qing
Q
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Floreancig
Paul E
PE
D000577:Amides / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D004987:Ethers; D009570:Nitriles / Q000737:chemistry*
D000577:Amides; D001643:Bridged Bicyclo Compounds; D004987:Ethers; D009570:Nitriles; C430593:cyanohydrin