94. Practical Asymmetric Diels-Alder Additions to Camphor-10-sulfonic-Acid-Derived Acrylates. Preliminary Communication
    Oppolzer, W.; Chapuis, C.; Kelly, M. J.
    Helv. Chim. Acta 1983, 66, 2358-2361

Starting from (+)-camphor-10-sulfonic acid (1) the chiral crystalline alcohols 3 and 11 were prepared in two steps. Lewis-acid-mediated [4+2]-additions of their acrylates to 1,3-dienes were studied. Notably, the crystalline acrylate 4 underwent TiCl₂ (OiPr)₂-promoted Diels-Alder addition to cyclopentadiene giving after recrystallization efficiently the pure (2R)-adduct 5.

DOI : 10.1002/hlca.19830660747