Abstract

Stereospecific metalation of (Z)- and (E)-1,4-decadiene with BuLi or BuLi-Me3COK followed by dimethoxyborylation and oxidn. gave (Z,E)-, (E,Z)-, and (E,E)-isomers of 2,4-decadien-1-ol (I), and the 4th isomer, (Z,Z)-I, was prepd. by hydrogenation of 2,4-decadiyn-1-ol. The isovalerates of all 4 I isomers and of (E,Z)-2,4-undecadien-1-ol were prepd. (E,Z)-I isovalerate is a natural flavor component. [on SciFinder (R)]

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