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

Date

1993-04-09

Author

FLORESCA, R
KURIHARA, M
WATT, DS
DEMIR, A

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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.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/67494

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo00060a040

Collections

Department of Chemistry, Article

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Citation Formats

R. FLORESCA, M. KURIHARA, D. WATT, and A. DEMIR, “CLEAVAGE OF UNSATURATED ALPHA-KETOLS TO OMEGA-OXO-ALPHA,BETA-UNSATURATED ACIDS,” JOURNAL OF ORGANIC CHEMISTRY, pp. 2196–2200, 1993, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/67494.