Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids

• DOI: 10.1021/acs.orglett.8b03551
• Publication Date: 2018-12-05T15:01:22Z
• Authors: Mostafa M. Amer; Ana C. Carrasco; Daniel J. Leonard; John W. Ward; Jonathan Clayden
• Keywords: Lactam; Carbonylation

Imidazolidinone derivatives of a range aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo mild Bischler–Napieralski-style cyclocarbonylation reaction that generates tricyclic lactam by insertion C═O group between amino acid nitrogen the ortho position aryl substituent. Regio- diastereoselective functionalization library substituted dihydroisoquinolinones their congeners in enantioenriched form.