Recoverable Chiral Sulfoxide: Asymmetric Diels–Alder Reaction Using Optically Active 1-(2-<i>p</i>-Tolylsulfinyl)pyrrolyl <i>α</i>,<i>β</i>-Unsaturated Ketones as a Dienophile

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Abstract

<jats:title>Abstract</jats:title> <jats:p>The Diels–Alder reaction of chiral cinnamoyl- and crotonyl(2-p-tolylsulfinyl)pyrrole with cyclopentadiene in the presence of AlCl3 or Yb(OTf)3 proceeded smoothly to give the corresponding endo adducts in excellent yield with high diastereoselectivity, ranging from 92 to 99% d.e. The chiral auxiliary, 2-pyrrolesulfoxide was efficiently recovered after alcoholysis of the adduct without loss of optical purity.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 26 (2), 145-146, 1997-02-01

    Oxford University Press (OUP)

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