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  • Title: Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents: Synthesis and Application to Asymmetric Diels-Alder Reaction.
    Author: Kitagawa O, Izawa H, Sato K, Dobashi A, Taguchi T, Shiro M.
    Journal: J Org Chem; 1998 Apr 17; 63(8):2634-2640. PubMed ID: 11672130.
    Abstract:
    New axially chiral N-acryl-N-allyl-o-tert-butylanilide and N-(o-tert-butylphenyl)-2-methylmaleimide with high optical purity and definite absolute configurations were prepared from o-tert-butylaniline and (S)-O-acetyl lactic acid or (R)-2-methylsuccinic acid, respectively. Iodine- or Lewis acid-mediated asymmetric Diels-Alder reaction of these axially chiral compounds with various dienes proceeded with high endo and diastereofacial selectivity.
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