Journal of Organic Chemistry p. 4348 - 4351 (1980)
Update date:2022-08-03
Topics:
Rinaldi, Peter L.
Levy, George C.
The synthesis and 13C NMR spectra of 1,2,3-decanetriol stereoisomers are described. High enantiomeric purity triols are obtained by chromatographic resolution of diastereomeric carbamates derived from 1-decyn-3-ol and (R)-1-(1-naphthyl)ethylamine. The triol is obtained by conversion of the acetylene to an olefin, stereoselective epoxidation with tert-butyl hydroperoxide and a transition-metal catalyst, and stereospecific ring opening of the epoxide with KOH.
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