Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed
Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived
Azomethine Ylides with Nitroalkenes
Version 2 2018-02-13, 06:30
Version 1 2018-01-31, 14:48
Posted on 2018-02-13 - 06:30
An organocatalytic
strategy for the synthesis of tetrasubstituted
pyrrolidines with monoactivated azomethine ylides in high enantiomeric
excess and excellent exo/endo selectivity is presented. The key to
success is the intramolecular activation via hydrogen bonding through
an o-hydroxy group, which allows the dipolar cycloaddition
to take place in the presence of azomethine ylides bearing only one
activating group. The intramolecular hydrogen bond in the azomethine
ylide and the intermolecular hydrogen bond with the catalyst have
been demonstrated by DFT calculations and mechanistic proofs to be
crucial for the reaction to proceed.
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Esteban, Francisco; Cieślik, Wioleta; Arpa, Enrique M.; Guerrero-Corella, Andrea; Díaz-Tendero, Sergio; Perles, Josefina; et al. (2018). Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed
Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived
Azomethine Ylides with Nitroalkenes. ACS Publications. Collection. https://doi.org/10.1021/acscatal.7b03553
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AUTHORS (9)
FE
Francisco Esteban
WC
Wioleta Cieślik
EA
Enrique M. Arpa
AG
Andrea Guerrero-Corella
SD
Sergio Díaz-Tendero
JP
Josefina Perles
JF
José A. Fernández-Salas
AF
Alberto Fraile
JA
José Alemán
KEYWORDS
intramolecular hydrogen bondorganocatalytic strategyintramolecular activationSalicylaldehyde-Derived Azomethine Ylidestetrasubstituted pyrrolidinesDFT calculationsazomethine ylidemonoactivated azomethine ylideshydroxy groupdipolar cycloadditionazomethine ylideshydrogen bondIntramolecular Hydrogen Bond Activation