One-Pot Synthesis of 1,2,3-Triols from Allylic Hydroperoxides and a Catalytic Amount of OsO4 in Aqueous Acetone

Alp C., ATMACA U., ÇELİK M., GÜLTEKİN M. S.

SYNLETT, no.17, pp.2765-2768, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: Issue: 17
  • Publication Date: 2009
  • Doi Number: 10.1055/s-0029-1217965
  • Journal Name: SYNLETT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2765-2768
  • Erzincan Binali Yildirim University Affiliated: Yes

Abstract

Allylic hydroperoxides were converted into the corresponding triols in the presence of a catalytic amount of OSO4. The present reaction involves regeneration of active osmium species by the hydroperoxide functionality and occurs in a diastereoselective manner to form triols in high yields. A plausible mechanism for the formation of 1,2,3-triols from allylic hydroperoxide is presented.