ChemInform Abstract: Palladium‐Catalyzed Intramolecular α‐Arylation of α‐Amino Acid Esters.

Abstract

2002 ring closure reactions ring closure reactions O 0130 -044Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters. -tert-Butyl-α-amino acid esters, substituted at the amino group with o-bromobenzyl or (o-bromophenyl)ethyl groups, undergo palladium-catalyzed ring-closure to isoindoline and tetrahydroisoquinoline carboxylic acid esters. The best results in the cyclization reactions are obtained using either ligands CPB or PPB in combination with Pd 2 (dba) 3 and tBuOLi as base. The reaction conditions are compatible with the Cbz protecting group at the nitrogen and the tert-butyl ester group. -(GAERTZEN, OLIVER; BUCHWALD, STEPHEN L.; J.

Intramolecular palladium-catalysed enolate arylation of 2- and 3-iodoindole derivatives for the synthesis of β-carbolines, γ-carbolines, and pyrrolo[3,4-b]indoles

“…During recent years, the palladium-catalysed arylation of enolate-type nucleophiles has received a great deal of attention. 13 In particular, the intramolecular version of these reactions [14][15][16][17][18] has found an increasing application in the synthesis of complex natural products. 19 Nevertheless, examples of these palladium-catalysed annulation processes involving haloindole substrates 20 are scarce and only feature the reactions of 4-haloindoles.…”