Work

Steric Course of the Rhodium-Catalyzed Decarbonylation of Chiral 4-M ethyl-[1-3H,2-2H1]pentanal

Year: 1987

Type: article

Abstract: (R)- and (S)-4-methyl-[1-3H,2-2H1]pentanal were prepared from L- and D-leucine via leucic acid and (S)- and (R)-4-methyl-[2-2H1]pentanoic acid. Decarbonylation of these samples with tris-(triphenylphosphine)rhodium chloride followed by Kuhn-Roth oxidation of the resulting 2-methylbutane gave chiral acetic acid of 35% e.e. S and 31% e.e. R configuration, respectively. The decarbonylation reaction thus proceeds with net retention of configuration, possibly accompanied by some racemization.

Source: Zeitschrift für Naturforschung C

DOI: 10.1515/znc-1987-0421

Authors: Hideaki Otsuka, Heinz G. Floss

Institution: The Ohio State University

Language: English

Topic: Asymmetric Hydrogenation and Catalysis

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $2,712

Funders: National Institutes of Health, National Institute of General Medical Sciences