CLEAVAGE OF UNSATURATED ALPHA-KETOLS TO OMEGA-OXO-ALPHA,BETA-UNSATURATED ACIDS

FLORESCA R., KURIHARA M., WATT D., DEMIR A.

JOURNAL OF ORGANIC CHEMISTRY, cilt.58, sa.8, ss.2196-2200, 1993 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 58 Sayı: 8
  • Basım Tarihi: 1993
  • Doi Numarası: 10.1021/jo00060a040
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2196-2200
  • Orta Doğu Teknik Üniversitesi Adresli: Hayır

Özet

Sodium periodate is a better reagent than sodium bismuthate, manganese dioxide, or lead tetraacetate for the cleavage of unsaturated alpha-ketols and affords omega-oxo-alpha,beta-unsaturated acids in good yield. The combination of this cleavage reaction and a rhodium(I)-mediated decarbonylation of omega-oxo-alpha,beta-unsaturated esters derived from polycyclic systems provided an enantioselective synthesis of cyclic systems bearing contiguous quaternary centers where one of the centers possessed gem-dimethyl groups.