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Enantioselective construction of a tetrasubstituted stereocenter in isoindolinones via an organocatalyzed reaction between ketones and 3-hydroxyisoindolinones

Matišić, Mateja; Gredičak, Matija (2021) Enantioselective construction of a tetrasubstituted stereocenter in isoindolinones via an organocatalyzed reaction between ketones and 3-hydroxyisoindolinones. Chemical Communications, 57 . pp. 13546-13547. ISSN 0022-4936

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Abstract

In a reaction catalyzed by a chiral phosphoric acid, ketones and in situ generated ketimines afford isoindolinone derivatives with a tetrasubstituted stereogenic center in high yields, and high diastereo- and enantioselectivities. An efficient enantioselective reaction between ketones and 3-hydroxyisoindolinones is described. In a reaction catalyzed by a chiral phosphoric acid, a broad range of ketones and in situ generated ketimines afforded isoindolinone derivatives comprising a tetrasubstituted stereocenter in high yields and enantioselectivities. The developed methodology is also suitable for the construction of compounds with vicinal stereogenic centers.

Item Type: Article
Uncontrolled Keywords: Enantioselective synthesis ; Organocatalysis ; Isoindolinones ; Ketones
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: 18 Jan 2022 11:09
URI: http://fulir.irb.hr/id/eprint/6876
DOI: 10.1039/d1cc05761h

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