摘要
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An efficient method has been developed for the first time for the synthesis of alpha,beta-unsaturated aldehydes with an (E)-trisubstituted C=C double bond by oxidation of mixtures of regio- and stereoisomeric allyl bromides withou...
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An efficient method has been developed for the first time for the synthesis of alpha,beta-unsaturated aldehydes with an (E)-trisubstituted C=C double bond by oxidation of mixtures of regio- and stereoisomeric allyl bromides without their preliminary separation. The substrates are available via ring opening of 1,2-disub-stituted cyclopropyl sulfonates. Allyl bromides containing additional functional groups were oxidized with N-methylmorpholine N-oxide more effectively. The reactions were carried out in solvents favoring nucleophilic substitution, and elevated temperature and prolonged reaction increased the fraction of the E isomer and reduced the amount of isomeric ketone.
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