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

Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement

Beilstein J Org Chem. 2019 Jul 12:15:1569-1574. doi: 10.3762/bjoc.15.160. eCollection 2019.

Authors

Gabrielle R Hammersley¹, Meghan F Nichol¹, Helena C Steffens¹, Jose M Delgado¹, Gesine K Veits¹, Javier Read de Alaniz¹

Affiliation

¹ Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, CA 93106-9510, USA.

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.

Grants and funding

S10 OD012077/OD/NIH HHS/United States