title: Solid-phase rhodium carbenoid N-H insertion reactions: the synthesis of a diverse array of indoles.
abstract: A solid-phase synthesis of an array of indoles is reported. The key step in our approach involves a N-H insertion reaction of N-alkylanilines into a highly reactive polymer-bound rhodium carbenoid intermediate to yield the corresponding alpha-arylamino-beta-ketoester. These insertion products were then treated under acid-catalyzed cyclodehydration conditions to yield a series of polymer-bound indole esters, which were subsequently cleaved from the resin under Lewis acid-promoted amidation conditions to yield the desired indoles in good yields and with excellent purities.
authors.affiliation: The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Sang-Hyeup
authors.initials: SH
authors.lastname: Lee
authors.forename: Bruce
authors.initials: B
authors.lastname: Clapham
authors.forename: Guido
authors.initials: G
authors.lastname: Koch
authors.forename: Jürg
authors.initials: J
authors.lastname: Zimmermann
authors.forename: Kim D
authors.initials: KD
authors.lastname: Janda
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D012117:Resins, Synthetic; D012238:Rhodium / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D007211:Indoles; D012117:Resins, Synthetic; D012238:Rhodium