1,3-Dipolar cycloadditions with azomethine ylide species generated from aminocyclopropanes

TETRAHEDRON

卷:74

Article

Wolan, Andrzej^1,2  Kowalska-Six, Justyna A.¹  Rajerison, Holisoa¹  Cesario, Michele¹  Cordier, Marie³  Six, Yvan^1,4 

[1] Univ Paris Saclay, Univ Paris Sud, CNRS UPR 2301, Inst Chim Subst Nat, 1 Av Terrasse, F-91198 Gif Sur Yvette, France

[2] Nicolaus Copernicus Univ, Fac Chem, Gagarina 7, PL-87100 Torun, Poland

[3] Univ Paris Saclay, Ecole Polytech, UMR CNRS 9138, LCM, F-91128 Palaiseau, France

[4] Univ Paris Saclay, Ecole Polytech, ENSTA, UMR CNRS 7652,LSO, F-91128 Palaiseau, France

关键词: Cyclopropane;    1,3-Dipolar cycloaddition;    Azomethine ylide;    Microwave-assisted synthesis;    Pyrrolizidine;    Titanium;   

DOI  :  10.1016/j.tet.2018.05.082

来源: Elsevier

【 摘 要 】

Two types of bicyclic N-cyclopropyl glycine ester derivatives have been prepared and put under scrutiny as possible precursors of azomethine ylides. The results demonstrate that they can indeed participate in 1,3-dipolar cycloaddition reactions with dipolarophiles, as illustrated in the cases of phenyl vinyl sulfone, N-phenylmaleimide, diethyl fumarate and diethyl maleate. The relative configurations of the major diastereoisomers produced are consistent with the predicted generation of azomethine ylide species, reacting in concerted cycloaddition processes. This unprecedented way of generating such 1,3-dipoles provides access to functionalised pyrrolizidine and pyrrolidine derivatives, that would be difficult to make directly by more classic methods. It was also found that using phenyl vinyl sulfone or N-phenylmaleimide as the dipolarophile reactant, a domino nucleophilic conjugate addition/1,3-dipolar cycloaddition process may operate competitively. (C) 2018 Elsevier Ltd. All rights reserved.

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