Recoverable Chiral Sulfoxide : Asymmetric Diels-Alder Reaction Usig Optically Active 1-(2-p-Tolylsulfinyl) pyrrolyl α, β-Unsaturated Ketones as a Dienophile
The Diels–Alder reaction of chiral cinnamoyl- and crotonyl(2-<I>p</I>-tolylsulfinyl)pyrrole with cyclopentadiene in the presence of AlCl<SUB>3</SUB> or Yb(OTf)<SUB>3</SUB> proceeded smoothly to give the corresponding <I>endo</I> 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.
- Chemistry letters
Chemistry letters 1997(2), 145-146, 1997-02
The Chemical Society of Japan