EFFECTIVE SYNTHESIS OF ENANTIOMERIC 2-PENTANOLS AND CHIRAL DOMINICALURES BASED ON THEM
The (S) and (R) enantiomers of sec-amyl-2-methyl-(2E)-pentenoate and 2,4-dimethyl-(2E)-pentenoate (dominicalure 1 and dominicalure 2 respectively), which are contained in the aggregation pheromone of the lesser grain borer Rhizopertha dominica, were synthesized by the acylation of (S)- and (R)-2-pentanols. (2S)-Pentanol was obtained in five stages with an overall yield of > 50percent from (S)-ethyl lactate with cross-coupling of the p-toluenesulfonate of (2S)-(2-tetrahydropyranyloxy)-1-propanol with lithium diethylcuprate at the key stage.Zinc chloride can be used as an effective catalyst for the removal of the tetrahydropyranyl protection under mild conditions. (2R)-Pentanol was prepared by inversion of the configuration of its (S) enantiomer by the Mitsunobu method.
Cheskis, B. A.,Shpiro, N. A.,Moiseenkov, A. M.
p. 1613 - 1616
(2007/10/02)
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