[2+1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines
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Title: | [2+1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines |
Author: | Padín Santos, Damián Cambeiro Cambeiro, Fermín Fañanás Mastral, Martín Varela Carrete, Jesús Ángel Saá Rodríguez, Carlos |
Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
Subject: | Carbenes | [2+1] Cycloaddition | Diazo compounds | Pyrrolidines | Ruthenium catalyst | |
Date of Issue: | 2016 |
Publisher: | American Chemical Society |
Citation: | Padín, D., Cambeiro, F., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2017). [2+1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines. ACS Catalysis, 7, 2, 992-996 |
Abstract: | Aza-alkynals undergo a cyclization reaction with diazo compounds in the presence of catalytic amounts of Cp*RuCl(cod) to afford vinyl epoxypyrrolidines, valuable building blocks for the synthesis of biologically active molecules. Ruthenium vinyl carbene intermediates have been invoked to explain the overall [2 + 1] cycloaddition (epoxy-annulation reaction). The reaction proceeds under mild conditions and in short reaction times (5–80 min) with complete (Z)- or (E)-stereoselectivity on the vinyl substituent, depending on the nature of the diazo compound used. Theoretical calculations support a mechanistic rationale to explain this controlled process. |
Description: | NOTICE: This is the peer reviewed version of the following article: Padín, D., Cambeiro, F., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2017). [2+1] Cycloaddition of Catalytic Ruthenium Vinyl Carbenes: A Stereoselective Controlled Access to (Z)- and (E)-Vinyl Epoxypyrrolidines. ACS Catalysis, 7, 2, 992-996. [doi: 10.1021/acscatal.6b02929]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving |
Publisher version: | https://doi.org/10.1021/acscatal.6b02929 |
URI: | http://hdl.handle.net/10347/23353 |
DOI: | 10.1021/acscatal.6b02929 |
E-ISSN: | 2155-5435 |
Rights: | Copyright © 2016 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving |
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