Novel Examples of the N-Methyl Effect on Cyclizations of N-BOC Derivatives of Amino Alcohols. A Theoretical Study
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New examples of the N-methyl effect on the cyclisation of N-tert-butoxycarbonyl derivatives of amino alcohols are reported. Ab initio studies for the displacement step with formation of the five-membered heterocycle indicate that the increase of the nucleophile character of the carbonyl oxygen of the carbamate group with the N-methyl substitution is responsible for the acceleration of the cyclisation step.
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Hamdach, A., El Hadrami, E. M., Testa, M. L., Gil, S., Zaballos-García, E., Sepúlveda-Arques, J., Arroyo, P., & Domingo, L. R. (2004). Novel examples of the N-methyl effect on cyclisations of N-Boc derivatives of amino alcohols. A theoretical study. En Tetrahedron (Vol. 60, Issue 52, pp. 12067-12073). Elsevier BV. https://doi.org/10.1016/j.tet.2004.10.038
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Elsevier BV
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