ChemInform Abstract: Flexible Synthesis of Planar Chiral Azoninones and Optically Active Indolizidinones.

Flexible Synthesis of Planar Chiral Azoninones and Optically Active Indolizidinones

The flexible synthesis of defined substituted optically active indolizidinones starting from chiral pool (S)-proline and trans 4-hydroxy-(S)-proline is described. Several defined 2-vinylpyrrolidines were generated in short sequences. The aza-Claisen rearrangement using chloro and phenylketene equivalents delivered nine-membered-ring lactams with up to three stereogenic centres and pS-arranged E olefins. Depending on the substitution pattern, certain azoninones had a flexible conformation and showed pS/pR double-bond flipping. Treatment of the unsaturated lactams with the soft electrophile iodine induced diastereoselective transannular ring contractions. Here, the planar chiral arrangement o…

CCDC 985005: Experimental Crystal Structure Determination

Related Article: Frank Bohland, Irina Erlin, Lukas Platte, Maike Schröder, Dieter Schollmeyer, Udo Nubbemeyer|2014|Eur.J.Org.Chem.|2014|6272|doi:10.1002/ejoc.201402720

CCDC 985006: Experimental Crystal Structure Determination

Related Article: Frank Bohland, Irina Erlin, Lukas Platte, Maike Schröder, Dieter Schollmeyer, Udo Nubbemeyer|2014|Eur.J.Org.Chem.|2014|6272|doi:10.1002/ejoc.201402720