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Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents:  Synthesis and Application to Asymmetric Diels−Alder Reaction

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journal contribution
posted on 28.03.1998 by Osamu Kitagawa, Hirotaka Izawa, Kiyonobu Sato, Akira Dobashi, Takeo Taguchi, Motoo Shiro
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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