188608-77-7Relevant articles and documents
Recoverable chiral sulfoxide: remote asymmetric induction in Lewis acid-promoted Diels-Alder reaction of chiral sulfinyl-substituted pyrrolyl α,β-unsaturated enones
Arai, Yoshitsugu,Masuda, Tsutomu,Masaki, Yukio
, p. 2165 - 2170 (2007/10/03)
1-[2-(p-Tolylsulfinyl)]pyrrolyl α,β-unsaturated enones served as efficient dienophiles in the Diels-Alder reaction, where the use of aluminium chloride or a lanthanide triflate effected the cycloaddition with cyclopentadiene, affording the endo adduct with high diastereoselectivity. In particular, for the sulfinyl dienophile, the chiral auxiliary (i.e. the sulfinyl pyrrole) was recovered after use without any loss of optical purity.
Recoverable chiral sulfoxide: Asymmetric diels-alder reaction using optically active 1-(2-p-tolylsulfinyl)pyrrolyl α,β-unsaturated ketones as a dienophile
Arai, Yoshitsugu,Masuda, Tsutomu,Masaki, Yukio
, p. 145 - 146 (2007/10/03)
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.
