Diastereoselective intramolecular Carbolithiations of Stereodefined Secondary Alkyllithiums Bearing a Remote Alkynylsilane

Simon, Meike; Karaghiosoff, Konstantin und Knochel, Paul (2018): Diastereoselective intramolecular Carbolithiations of Stereodefined Secondary Alkyllithiums Bearing a Remote Alkynylsilane. In: Organic Letters, Bd. 20, Nr. 12: S. 3518-3521

Abstract

Various secondary alkyl iodides bearing a remote alkynylsilane underwent intramolecular carbolithiations triggered by an I/Li-exchange performed at -100 degrees C using t-BuLi (2.5 equiv). The resulting alkenyllithiums were stereo selectively converted to tetrasubstituted cyclopentane exo-alkylidenes. After Pd-catalyzed hydrogenation, cyclopentanes and cis-bicyclo[4.3.0]nonanes were obtained with stereo control of four contiguous centers.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1523-7060
• Sprache: Englisch