Recoverable Chiral Sulfoxide

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...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry letters 1997-02, Vol.26 (2), p.145
Main Authors: Arai, Yoshitsugu, Masuda, Tsutomu, Masaki, Yukio
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0366-7022
1348-0715