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Angnes RA, Oliveira JM, Oliveira CC, et al. Stereoselective synthesis of aryl cyclopentene scaffolds by Heck-Matsuda desymmetrization of 3-cyclopentenol. Chemistry. 2014;20(41):13117-21doi: 10.1002/chem.201404159.
Angnes, R. A., Oliveira, J. M., Oliveira, C. C., Martins, N. C., & Correia, C. R. (2014). Stereoselective synthesis of aryl cyclopentene scaffolds by Heck-Matsuda desymmetrization of 3-cyclopentenol. Chemistry (Weinheim an der Bergstrasse, Germany), 20(41), 13117-21. https://doi.org/10.1002/chem.201404159
Angnes, Ricardo A, et al. "Stereoselective synthesis of aryl cyclopentene scaffolds by Heck-Matsuda desymmetrization of 3-cyclopentenol." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,41 (2014): 13117-21. doi: https://doi.org/10.1002/chem.201404159
Angnes RA, Oliveira JM, Oliveira CC, Martins NC, Correia CR. Stereoselective synthesis of aryl cyclopentene scaffolds by Heck-Matsuda desymmetrization of 3-cyclopentenol. Chemistry. 2014 Oct 06;20(41):13117-21. doi: 10.1002/chem.201404159. Epub 2014 Aug 26. PMID: 25155478.
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Chemistry. 2014 Oct 06;20(41):13117-21. doi: 10.1002/chem.201404159. Epub 2014 Aug 26.

Stereoselective synthesis of aryl cyclopentene scaffolds by Heck-Matsuda desymmetrization of 3-cyclopentenol.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ricardo A Angnes, Juliana M Oliveira, Caio C Oliveira, Nelson C Martins, Carlos Roque D Correia

Affiliations

  1. Institute of Chemistry, State University of Campinas- Unicamp, C.P. 6154, CEP. 13083-970, Campinas, São Paulo (Brazil) www.correia-group.com.

PMID: 25155478 DOI: 10.1002/chem.201404159

Abstract

A new enantioselective Heck-Matsuda desymmetrization reaction was accomplished by using 3-cyclopentenol to produce chiral five-membered 4-aryl cyclopentenol scaffolds in good yields and high ee's, together with some 3-aryl-cyclopentanones as minor products. Mechanistically, the hydroxyl group of 3-cyclopentenol acts as a directing group and is responsible for the cis- arrangement in the formation of the 4-aryl-cyclopentenols.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Heck reaction; aryldiazonium salts; chiral N,N ligands; desymmetrization; palladium

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