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n-BuLi/LiCH2CN-Mediated One-Carbon Homologation of Aryl Epoxides into Conjugated Allyl Alcohols

Takashi Tomioka*, Rambabu Sankranti, Tsuyoshi Yamada and Courtney Clark

*Department of Chemistry and Biochemistry, University of Mississippi, University, Mississippi 38677, United States, Email:

T. Tomioka, R. Sankranti, T. Yamada, C. Clark, Org. Lett., 2013, 15, 5099-5101.

DOI: 10.1021/ol402466y


In the presence of a 1:1 mixture of n-butyllithium and lithioacetonitrile in THF, a series of styrene oxides can be converted into one-carbon homologated allyl alcohols in an unusual regioselective manner.

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Key Words

terminal alkenes, allyl alcohols

ID: J54-Y2013