title: Ketosulfonyl indoles in the regiodefined synthesis of tryptophols and related indole derivatives.
abstract: Reduction of ketosulfonyl indoles with sodium borohydride provides a ready entry to tryptophols in a regiocomplementary fashion with respect to the traditional oxirane ring-opening by indoles under Friedel-Crafts conditions. Compared to traditional β-ketosulfones, ketosulfonyl indoles show a peculiar behavior since they undergo a Lewis acid promoted elimination of the arylsulfonyl group allowing the preparation of indolyl-substituted 1,4-dicarbonyl derivatives.
authors.affiliation: School of Science and Technology, Chemistry Division, Università di Camerino, via S. Agostino, 1 I-62032 Camerino, Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Palmieri
authors.forename: Marino
authors.initials: M
authors.lastname: Petrini
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D000438:Alcohols
chemical_list: D007211:Indoles; D007659:Ketones; C005949:tryptophol; D000438:Alcohols