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


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

JOURNAL OF ORGANIC CHEMISTRY, vol.58, no.8, pp.2196-2200, 1993 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 8
  • Publication Date: 1993
  • Doi Number: 10.1021/jo00060a040
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.2196-2200

Abstract

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.