title: Asymmetric cascade reaction to allylic sulfonamides from allylic alcohols by palladium(II)/base-catalyzed rearrangement of allylic carbamates.
abstract: A regio- and enantioselective tandem reaction is reported capable of directly transforming readily accessible achiral allylic alcohols into chiral sulfonyl-protected allylic amines. The reaction is catalyzed by the cooperative action of a chiral ferrocene palladacycle and a tertiary amine base and combines high step-economy with operational simplicity (e.g. no need for inert-gas atmosphere or catalyst activation). Mechanistic studies support a Pd(II)-catalyzed [3,3] rearrangement of allylic carbamates--generated in situ from the allylic alcohol and an isocyanate--as the key step, which is followed by a decarboxylation.
authors.affiliation: Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany) http://www.peters.oc.uni-stuttgart.de.
authors.forename: Johannes Moritz
authors.initials: JM
authors.lastname: Bauer
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Frey
authors.forename: René
authors.initials: R
authors.lastname: Peters
keywords: Brønsted bases; Lewis acids; domino reactions; palladacycles; sulfonamides