Sie befinden Sich nicht im Netzwerk der Universität Paderborn. Der Zugriff auf elektronische Ressourcen ist gegebenenfalls nur via VPN oder Shibboleth (DFN-AAI) möglich. mehr Informationen...
Synthesis of [alpha]-Chiral Butyrolactones by Highly Stereoselective Radical Transfer or Sequential Asymmetric Alkylations: Concise Preparation of Leupyrrin Moieties
Ist Teil von
Chemistry : a European journal, 2015-11, Vol.21 (45), p.16266
Ort / Verlag
Weinheim: Wiley Subscription Services, Inc
Erscheinungsjahr
2015
Quelle
Wiley Online Library
Beschreibungen/Notizen
Inspired by the bioactive natural metabolites leupyrrinA1 and B1, two novel stereoselective methods for the highly concise synthesis of densely substituted [alpha]-chiral butyrolactones are reported. The first approach relies on an innovative three-step TiIII-catalyzed radical reaction that proceeds with excellent chemo-, regio-, and stereoselectivity. The alternative route utilizes sequential asymmetric alkylations and enables asymmetric synthesis of the authentic [alpha]-tetrasubstituted butyrolactone motif of the leupyrrins in only four steps from commercially available substrates.