Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement

Gabrielle R. Hammersley; Meghan F. Nichol; Helena C. Steffens; Jose M. Delgado; Gesine K. Veits; Javier Read de Alaniz

doi:10.3762/bjoc.15.160

Beilstein Journal of Organic Chemistry (Jul 2019)

Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement

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

Affiliations

Gabrielle R. Hammersley: Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA 93106-9510, USA
Meghan F. Nichol: Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA 93106-9510, USA
Helena C. Steffens: Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA 93106-9510, USA
Jose M. Delgado: Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA 93106-9510, USA
Gesine K. Veits: Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA 93106-9510, USA
Javier Read de Alaniz: Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA 93106-9510, USA

DOI: https://doi.org/10.3762/bjoc.15.160
Journal volume & issue: Vol. 15, no. 1
pp. 1569 – 1574

Abstract

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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.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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