The selectivity of iodoetherification of N-substituted 3-aminopent-4-en-1-ols 1, providing mixtures of N-substituted (E)-and (E)-3-amino-2-iodomethyltetrahydrofurans [(Z)-2 and (E)-2], correlates well with the electronic effects of the N-substituents, increasing with an increase in the electron withdrawing effect of the substituents.
Y. Tamaru, H. Harayama and T. Bando, J. Chem. Soc., Chem. Commun., 1993, 1601 DOI: 10.1039/C39930001601
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