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

Alp, Cemalettin; Atmaca, Ufuk; Çelik, Murat; Gültekin, Mehmet

doi:10.1055/s-0029-1217965

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

Alp C., Atmaca U., Çelik M., Gültekin M. S.

SYNLETT, sa.17, ss.2765-2768, 2009 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Basım Tarihi: 2009
Doi Numarası: 10.1055/s-0029-1217965
Dergi Adı: SYNLETT
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.2765-2768
Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
Atatürk Üniversitesi Adresli: Evet

Özet

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.