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Paper | Regular issue | Vol 26, No. 9, 1987, pp.2461-2468
Published online, 1st January, 1970
DOI: 10.3987/R-1987-09-2461
Chiral Synthesis of (R)-(+)-Citronellal via Stereoselective Protonation

Seiichi Takano, Hiroyuki Chiba, Junko Kudo, Michiyasu Takahashi, and Kunio Ogasawra

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Protonation of the enolates (8) and (12) generated from an epimeric mixture of the α,γ-disubstituted γ-lactone (7) is shown to yield the syn-α/γ-disubstituted γ-lactone (10) predominant over the anti-α/γ-disubstituted γ-lactone (11). When the silyl enol ether (12) generated in situ is protonated with trifluoroacetic acid, the best selectivity is obtained. The syn-epimer (10) thus obtained is converted into (R)-(+)-citronellal (17) in four steps of reactions.