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Cu(I)‑Catalyzed Asymmetric [3 + 2] Cycloaddition of Azomethine 2 Ylides with Cyclobutenones
Metadatos
Title:Cu(I)‑Catalyzed Asymmetric [3 + 2] Cycloaddition of Azomethine 2 Ylides with Cyclobutenones
Author:Corpas, Javier; Ponce, Alberto; Adrio, Javier; Carretero, Juan C.
Entity:UAM. Departamento de Química Orgánica; UAM. Instituto de Investigación Avanzada en Ciencias Químicas (IAdChem)
UAM Author:Corpas Pardo, Javier ; Carretero Gonzálvez, Juan Carlos ; Adrio Sevilla, Francisco Javier ; Ponce, Gustavo Alberto
Publisher:American Chemical Society
Date:2018-05
Citation:
10.1021/acs.orglett.8b00936
Organic Letters 20.11 (2018): 3179-3182
ISSN:1523-7060 (print); 1523-7052 (online)
DOI:10.1021/acs.orglett.8b00936
Funded by:Financial support of this work by the Ministerio de Economía, Industria y Competitividad
and Fondo Europeo de Desarrollo Regional (Project Nos. CTQ2012-35790 MINECO and
CTQ2015-66954-P MINECO/FEDER, UE) is gratefully acknowledged. A.P. thanks the MICINN for a predoctoral fellowship. J.C. thanks the MECD for a FPU predoctoral
fellowship
Project:Gobierno de España. CTQ2012-35790; Gobierno de España. CTQ2015-66954-P
The catalytic asymmetric 1,3-dipolar cycloaddition of cyclobutenones with azomethine ylides provides straightforward access to densely substituted 3-azabicyclo[3.2.0]heptanes. In the presence of CuI/(R)-Fesulphos as the catalytic system, high levels of diastereoselectivity and enantioselectivity were achieved (up to 98% enantiomeric excess (ee)).