ChemInform Abstract: Recoverable Chiral Sulfoxide: Remote Asymmetric Induction in Lewis Acid-Promoted Diels—Alder Reaction of Chiral Sulfinyl-Substituted Pyrrolyl α,β-Unsaturated Enones.

✍ Scribed by Yoshitsugu Arai; Tsutomu Masuda; Yukio Masaki

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199944045

✦ Synopsis

Recoverable Chiral Sulfoxide: Remote Asymmetric Induction in Lewis Acid-Promoted Diels-Alder Reaction of Chiral Sulfinyl-Substituted Pyrrolyl α,β-Unsaturated Enones.

-Stereoselective Diels-Alder reactions in the presence of AlCl 3 or Sm(O-Tf) 3 yield 96-99% of endo-enriched product mixtures which are recrystallized or purified by HPLC to give the endo adducts (III) with 96-98% d.e. (no yields given).