• Medientyp: E-Artikel
  • Titel: Asymmetric Induction in the Diels‐Alder Reaction of Chiral (2S)‐2‐(tert‐Butyl)‐5‐methylene‐1,3‐dioxolan‐4‐one
  • Beteiligte: Mattay, Jochen; Mertes, Jürgen; Maas, Gerhard
  • Erschienen: Wiley, 1989
  • Erschienen in: Chemische Berichte, 122 (1989) 2, Seite 327-330
  • Sprache: Englisch
  • DOI: 10.1002/cber.19891220220
  • ISSN: 0009-2940
  • Schlagwörter: Inorganic Chemistry
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  • Anmerkungen:
  • Beschreibung: AbstractThe Diels‐Alder reaction of the cyclic methylene compound 3 with cyclopentadiene at ambient temperature leads to the adducts 4 and 5 with more than 95% face and more than 96% exo selectivity. The structure of the products has been verified by chemical correlation as well as by X‐ray diffraction analysis of the Diels‐Alder adduct 4. The mixture of 4 and 5 was converted to optically active (+)‐norbornenone 12. face Selectivity was dramatically decreased by Lewis acid catalysis with TiCl2(iPrO)2 or AlEtCl2 at lower temperatures.