76. Asymmetric induction in Diels-Alder reactions to acrylates derived from chiral sec-alcohols. Preliminary communication
    Oppolzer, W.; Kurth, M.; Reichlin, D.; Chapuis, C.; Mohnhaupt, M.; Moffatt, F.
    Helv. Chim. Acta 1981, 64, 2802-2807

Starting from the enantiomerically pure monoterpenes (+)-pulegone (3), (+)-limonene (7), (−)-β-pinene (9), (+)- and (−)-camphor (13) or (+)-cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl₄-promotedDiels-Alder addition to cyclopentadiene (Scheme 3, Table) giving in a predictable manner either the (2R)- or the (2S)-adducts III with 63 to 88% asymmetric induction.

DOI : 10.1002/hlca.19810640841