Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents: Synthesis and Application to Asymmetric Diels−Alder Reaction
journal contributionposted on 28.03.1998 by Osamu Kitagawa, Hirotaka Izawa, Kiyonobu Sato, Akira Dobashi, Takeo Taguchi, Motoo Shiro
Any type of content formally published in an academic journal, usually following a peer-review process.
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.