Cleavage of Unsaturated α-Ketols to ω-Oxo-α,β-unsaturated Acids

Rey Floresca, Masaaki Kurihara, David S. Watt, Ayhan Demir

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

Sodium periodate is a better reagent than sodium bismuthate, manganese dioxide, or lead tetraacetate for the cleavage of unsaturated α-ketols and affords ω-oxo-α,β-unsaturated acids in good yield. The combination of this cleavage reaction and a rhodium(I)-mediated decarbonylation of ω-oxo-α,β-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.

Original languageEnglish
Pages (from-to)2196-2200
Number of pages5
JournalJournal of Organic Chemistry
Volume58
Issue number8
DOIs
StatePublished - 1993

ASJC Scopus subject areas

  • Organic Chemistry

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