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Arpa EM, González-Esguevillas M, Pascual-Escudero A, et al. Catalytic Asymmetric Synthesis of Bicycloprolines by a 1,3-Dipolar Cycloaddition/Intramolecular Alkylation Strategy. J Org Chem. 2016;81(14):6128-35doi: 10.1021/acs.joc.6b01100.
Arpa, E. M., González-Esguevillas, M., Pascual-Escudero, A., Adrio, J., & Carretero, J. C. (2016). Catalytic Asymmetric Synthesis of Bicycloprolines by a 1,3-Dipolar Cycloaddition/Intramolecular Alkylation Strategy. The Journal of organic chemistry, 81(14), 6128-35. https://doi.org/10.1021/acs.joc.6b01100
Arpa, Enrique M, et al. "Catalytic Asymmetric Synthesis of Bicycloprolines by a 1,3-Dipolar Cycloaddition/Intramolecular Alkylation Strategy." The Journal of organic chemistry vol. 81,14 (2016): 6128-35. doi: https://doi.org/10.1021/acs.joc.6b01100
Arpa EM, González-Esguevillas M, Pascual-Escudero A, Adrio J, Carretero JC. Catalytic Asymmetric Synthesis of Bicycloprolines by a 1,3-Dipolar Cycloaddition/Intramolecular Alkylation Strategy. J Org Chem. 2016 Jul 15;81(14):6128-35. doi: 10.1021/acs.joc.6b01100. Epub 2016 Jul 05. PMID: 27322168.
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J Org Chem. 2016 Jul 15;81(14):6128-35. doi: 10.1021/acs.joc.6b01100. Epub 2016 Jul 05.

Catalytic Asymmetric Synthesis of Bicycloprolines by a 1,3-Dipolar Cycloaddition/Intramolecular Alkylation Strategy.

The Journal of organic chemistry

Enrique M Arpa, María González-Esguevillas, Ana Pascual-Escudero, Javier Adrio, Juan C Carretero

Affiliations

  1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid , Cantoblanco, 28049 Madrid, Spain.

PMID: 27322168 DOI: 10.1021/acs.joc.6b01100

Abstract

The diastereoselective one-pot synthesis of hexahydrocyclopenta[b]pyrrole derivatives (bicycloprolines) has been achieved by base-mediated reactions of (E)-tert-butyl 6-bromo-2-hexenoate with α-imino esters. The catalytic asymmetric version of this process has been efficiently achieved using the Cu(I)/(R)-DTBM-Segphos complex as a catalyst following a two-step 1,3-dipolar cycloaddition/intramolecular alkylation sequence.

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