Computational Investigation of the Aza-Cope Rearrangement Leading to Angularly Substituted 1-Azabicyclic Rings

Ricardo Meyrelles; Yener Fetisleam; Boris Maryasin

doi:10.1055/a-1946-6578

Synlett, Table of Contents

Synlett 2023; 34(05): 437-440
DOI: 10.1055/a-1946-6578

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Computational Investigation of the Aza-Cope Rearrangement Leading to Angularly Substituted 1-Azabicyclic Rings

Ricardo Meyrelles

^aInstitute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria

^bInstitute of Theoretical Chemistry, University of Vienna, Währinger Straße 17, 1090 Vienna, Austria

^cVienna Doctoral School in Chemistry, University of Vienna, Währinger Straße 42, 1090 Vienna, Austria

,

Yener Fetisleam

^bInstitute of Theoretical Chemistry, University of Vienna, Währinger Straße 17, 1090 Vienna, Austria

,

Boris Maryasin ∗

^aInstitute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria

^bInstitute of Theoretical Chemistry, University of Vienna, Währinger Straße 17, 1090 Vienna, Austria

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Abstract

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Abstract

A computational study of the aza-Cope rearrangement leading to angularly substituted 1-azabicyclic ring systems is presented. The calculations estimate the probability of the proton transfer between reaction intermediates and protic solvents, explain the experimentally observed reaction selectivity, and suggest new potentially more efficient systems for further in vitro and in silico investigations.

Key words

aza-Cope rearrangement - DFT - reaction mechanisms - sigmatropic rearrangements - proton transfer - cis–trans selectivity

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References

References and Notes
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