Jump to Main Content
- Montgomery, T. Patrick; Hassan, Abbas; Park, Boyoung Y.; Krische, Michael J.
- Journal of the American Chemical Society 2012 v.134 no.27 pp. 11100-11103
- alcohols; aldehydes; bromination; catalysts; chemical bonding; enantiomers; hydrogenation; iridium
- ... Upon exposure of acrylic ester 1 to alcohols 2a–i in the presence of a cyclometalated iridium catalyst modified by (−)-TMBTP, catalytic C–C coupling occurs, providing enantiomerically enriched 5-substituted α-exo-methylene γ-butyrolactones 3a–i. Bromination of the methylene butyrolactone products followed by zinc-mediated reductive aldehyde addition provides the disubstituted α-exo-methylene γ-but ...
- PubMed Central:
- Duangdee, Nongnaphat; Harnying, Wacharee; Rulli, Giuseppe; Neudörfl, Jörg-M.; Gröger, Harald; Berkessel, Albrecht
- Journal of the American Chemical Society 2012 v.134 no.27 pp. 11196-11205
- X-radiation; X-ray diffraction; acids; alcohols; ammonium chloride; catalysts; enantiomers; high performance liquid chromatography; monitoring; solvents
- ... Aldol reactions with trifluoroacetophenones as acceptors yield chiral α-aryl, α-trifluoromethyl tertiary alcohols, valuable intermediates in organic synthesis. Of the various organocatalysts examined, Singh’s catalyst [(2S)-N-[(1S)-1-hydroxydiphenylmethyl-3-methylbutyl]-2-pyrrolidinecarboxamide] was found to efficiently promote this organocatalytic transformation in a highly enantioselective manne ...