ChemInform Abstract: SmI₂‐Promoted Intra‐ and Intermolecular C—C Bond Formation with Chiral N‐Acyl Oxazolidinones.

Abstract

C-C bond formation O 0282SmI2-Promoted Intra-and Intermolecular C-C Bond Formation with Chiral N-Acyl Oxazolidinones. -Ketones (I) and (IV) bearing a chiral oxazolidinone moiety react with acrylamides to give acyclic chiral ketones. The C-C bond formation is accompanied by removal of the oxazolidinone moiety. Intramolecular cyclizations are also performed with the same type of substrates to give trans-disubstituted cyclopentanones. Attempts to cyclize heteroatom-containing analogues are less successful. -(TAANING, R. H.; THIM, L.; KARAFFA, J.; CAMPANA, A. G.; HANSEN, A.-M.; SKRYDSTRUP*, T.; Tetrahedron 64 (2008) 52, 11884-11895; Dep. Chem., Univ. Aarhus, DK-8000 Aarhus, Den.; Eng.) -Klein 21-041