Regiochemical control of the ring-opening of 1, 2-epoxides by means of chelating processes. Synthesis and reactions of the cis-and trans-oxides derived from 4-( …

…, P Crotti, LA Flippin, F Macchia

文献索引：Chini, Marco; Crotti, Paolo; Flippin, Lee A.; Macchia, Franco Journal of Organic Chemistry, 1990 , vol. 55, # 14 p. 4265 - 4272

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被引用次数: 44

摘要

The synthesis and reactions of diastereomeric epoxides cis-1 and trans-2 with heteronucleophiles were carried out in order to probe the effect of remote polar functionality on the regioselectivity of nucleophilic addition to the epoxide ring. The reaction of cis- epoxide 1 with T ic 4 in CH2C12 gave exclusively the chlorohydrin 7, whereas the regioisomeric chlorohydrin 6 was obtained as the main product from the reaction of 1 with ...