Epoxide 2 was prepared from 3, 4-dichloro-1-butene (1) by epoxidation with m-CPBA and subsequent dehydrohalogenation of the intermediate dichloroepoxide with molten KOH, affording 2 in 64% overall yield (2 steps). Catalytic CuBr/SMe2-mediated SN2'addition of sp2-or sp3-hybridized Grignard reagents to 2-chloro-3, 4-epoxy-1-butene (2) afforded (Z)-3- chloroallylic alcohols such as 3 in good yields and with high regio-and stereoselectivity.
[Shellhamer, Dale F.; Green, Richard C.; Luttrull, Jeffrey K.; Seneker, Stephan D.; Potter, Mark K.; et al. Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 229 - 232]
