Gezielte Hydroxylierung von Allylstellungen

Treatment of a-pinene with Me3COK and BuLi gave intermediate I which was oxidized with H2O2 to give 42% (1S,5R)-myrtenol (II, X = OH) and .apprx.1% (1R,3R,5S)-trans-pinocarveol (III, X = OH). Treatment of I with ethylene oxide gave 25% II(X = CH2CH2OH) and 13% III (X = CH2CH2OH). (E)-MeCH:CHCH2K treated with FB(OMe)2 gave intermediate MeCH:CHCH2B(OMe)2 which was oxidized with H2O2 to give 50% Z-MeCH:CHCH2OH, 2% E-MeCH:CHCH2OH, and 7% H2C:CHCH(OH)Me. Analogously obtained was 58% Z-MeCH:CMeCH2OH. [on SciFinder (R)]


Published in:
Helvetica Chimica Acta, 58, 4, 1094-9
Year:
1975
Keywords:
Note:
CAN 84:17562
30-10
Terpenoids
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0018-019X
written in German.
547-61-5P; 57586-79-5P; 57606-36-7P Role: FORM (Formation, nonpreparative), PREP (Preparation) (formation of, in hydroxylation of (+)-a-pinene); 513-35-9; 624-64-6; 7785-70-8 Role: RCT (Reactant), RACT (Reactant or reagent) (hydroxylation of); 367-46-4 Role: RCT (Reactant), RACT (Reactant or reagent) (hydroxylation of terpenes and alkenes in presence of); 6712-78-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, by hydroxylation of (+)-a-pinene); 4088-60-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, from (E)-2-butene hydroxylation of, in presence of fluorodimethoxyborane); 4435-54-5P; 19319-26-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, from 2-methyl-2-butene)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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