Solvent-induced stereospecific isomerization of an allylic alcohol to a homoallylic alcohol catalyzed by a chiral lithium amide

PI Arvidsson, M Hansson, AZQ Khan…

文献索引：Arvidsson, Per I.; Hansson, Maria; Khan, Agha Zul-Qarnain; Ahlberg, Per Canadian Journal of Chemistry, 1998 , vol. 76, # 6 p. 795 - 799

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被引用次数: 9

摘要

Deprotonation of cyclohexene oxide, 1, by lithium (S)-2-(1-pyrrolidinylmethyl) pyrrolidide, 2- Li, on changing the solvent from tetrahydrofuran (THF) to, for example, 2, 5- dimethyltetrahydrofuran (DMTHF) or diethyl ether (DEE) has been shown to yield, besides the lithium alkoxide of 2-cyclohexene-1-ol, 3-Li, the lithium alkoxide of the homoallylic alcohol 3-cyclohexene-1-ol, 4-Li. It was shown that compound 4-Li is formed from 3-Li. No ...