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Construction of chiral Betti base precursors containing a congested quaternary stereogenic center via chiral phosphoric acid-catalyzed arylation of isoindolinone-derived ketimines

Glavač, Danijel; Gredičak, Matija (2022) Construction of chiral Betti base precursors containing a congested quaternary stereogenic center via chiral phosphoric acid-catalyzed arylation of isoindolinone-derived ketimines. New Journal of Chemistry, 46 (18). pp. 8760-8764. ISSN 1144-0546

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Abstract

Synthesis of enantioenriched Betti base precursors containing a congested quaternary stereocenter is described. In a chiral phosphoric acid-catalyzed reaction, a series of in situ generated isoindolinone- derived ketimines and phenol derivatives yield products in good to excellent yields, and moderate enantioselectivities. Conversion of the obtained products into chiral Betti bases with the retention of the optical purity is demonstrated.

Item Type: Article
Uncontrolled Keywords: Friedel-Crafts reaction ; electron-rich phenols ; enantioselective construction ; asymmetric-synthesis ; aminonaphthols ; 2-naphthols ; naphthols ; ligands
Subjects: NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Nove strategije za pripravu tetrasupstituiranih kiralnih centara: asimetrične katalitičke reakcije usmjerene protuanionom-NSYNC-ACDCMatija GredičakIP-2018-01-4053HRZZ
Depositing User: Matija Gredičak
Date Deposited: 02 Nov 2022 15:14
URI: http://fulir.irb.hr/id/eprint/7581
DOI: 10.1039/d2nj00493c

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