Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2019 Jul 12:15:1569-1574.
doi: 10.3762/bjoc.15.160. eCollection 2019.

Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement

Gabrielle R Hammersley  1 , Meghan F Nichol  1 , Helena C Steffens  1 , Jose M Delgado  1 , Gesine K Veits  1 , Javier Read de Alaniz  1
Affiliations

Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement

Gabrielle R Hammersley et al. Beilstein J Org Chem. .

Abstract

An enantioselective aza-Piancatelli rearrangement has been developed using a chiral Brønsted acid based on pentacarboxycyclopentadiene (PCCP). This reaction provides rapid access to valuable chiral 4-amino-2-cyclopentenone building blocks from readily available starting material and is operationally simple.

Keywords: Brønsted acid; PCCP; aza-Piancatelli; cyclopentane; furylcarbinols.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Proposed mechanism of the asymmetric aza-Piancatelli reaction.
Scheme 1
Scheme 1
Asymmetric aza-Piancatelli rearrangement with a range of substituted anilines. *To simplify the purification process, carboxylic acids were transformed in situ into the corresponding methyl ester using (trimethylsilyl)diazomethane.
Scheme 2
Scheme 2
Asymmetric aza-Piancatelli rearrangement with a range of substituted furylcarbinols. *To simplify the purification process, carboxylic acids were transformed in situ into the corresponding methyl ester using (trimethylsilyl)diazomethane.
See this image and copyright information in PMC

References

    1. Liu G, Shirley M E, Van K N, McFarlin R L, Romo D. Nat Chem. 2013;5:1049–1057. doi: 10.1038/nchem.1788. - DOI - PMC - PubMed
    1. Heasley B. Curr Org Chem. 2014;18:641–686. doi: 10.2174/13852728113176660150. - DOI
    1. Köck M, Grube A, Seiple I B, Baran P S. Angew Chem, Int Ed. 2007;46:6586–6594. doi: 10.1002/anie.200701798. - DOI - PubMed
    1. Seiple I B, Su S, Young I S, Lewis C A, Yamaguchi J, Baran P S. Angew Chem, Int Ed. 2010;49:1095–1098. doi: 10.1002/anie.200907112. - DOI - PMC - PubMed
    1. Trost B M, Dong G. J Am Chem Soc. 2006;128:6054–6055. doi: 10.1021/ja061105q. - DOI - PMC - PubMed