Chiral phosphoric acid-catalyzed Friedel-Crafts reaction of 2,5-disubstituted and 2-monosubstituted pyrroles with isoindolinone-derived ketimines

Beriša, Arben; Gredičak, Matija (2023) Chiral phosphoric acid-catalyzed Friedel-Crafts reaction of 2,5-disubstituted and 2-monosubstituted pyrroles with isoindolinone-derived ketimines. Organic and Biomolecular Chemistry, 21 . pp. 3381-3387. ISSN 2325-2170

Preview

PDF - Published Version - article Download (1MB) | Preview

Abstract

Enantioselective reaction between 2,5-disubstituted pyrroles and diaryl-ketimines, generated in situ from isoindolinone-derived alcohols, is described. Pyrrole derivatives possessing congested tetrasubstituted stereogenic center in β-(C3) position are generally obtained in high yields and enantioselectivities. The transformation can be extended to 2-monosubstituted pyrroles, generating chiral α-(C5) functionalized pyrrole products. Control experiments were conducted In order to elucidate origins of low enantioselectivities observed in some of the products.

Item Type:	Article
Uncontrolled Keywords:	-
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Nove strategije za pripravu tetrasupstituiranih kiralnih centara: asimetrične katalitičke reakcije usmjerene protuanionom-NSYNC-ACDC Matija Gredičak IP-2018-01-4053 HRZZ
Depositing User:	Matija Gredičak
Date Deposited:	23 Jun 2023 10:47
URI:	http://fulir.irb.hr/id/eprint/8038
DOI:	10.1039/d3ob00326d

Actions (login required)

View Item