Asymmetric Induction in Diels-Alder Reactions to Acrylates Derived from Chiral sec-Alcohols

Article abstract of DOI:10.1002/hlca.19810640841

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 and 18 were prepared; their acrylates II underwent a TiCl4-promoted Diels-Alder addition to cyclopentadiene (Scheme 3, Table) giving in a predictable manner either the (2R)- or the (2S)-adducts III with 63 to 88percent asymmetric induction.