Novel examples of the N-methyl effect on cyclisations of N-Boc derivatives of amino alcohols. A theoretical study

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 t...

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Bibliographic Details
Published in:Tetrahedron 2004-12, Vol.60 (52), p.12067-12073
Main Authors: Hamdach, A., El Hadrami, E.M., Testa, M.L., Gil, S., Zaballos-García, E., Sepúlveda-Arques, J., Arroyo, P., Domingo, L.R.
Format: Article
Language:English
Subjects:
Amino alcohols
Cyclocarbamation
Thorpe–Ingold effect
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Summary: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. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.10.038