• Something wrong with this record ?

Axially chiral dimethylaminobenzimidazoles and their preliminary evaluation as acyl-transfer reagents

D. Toman, I. Nemec, O. Kurka, A. Přibylka, P. Cankař

. 2025 ; 23 (11) : 2672-2682. [pub] 20250312

Status not-indexed Language English Country England, Great Britain

Document type Journal Article

Persistent link   https://www.medvik.cz/link/bmc25008241

The synthesis of axially chiral benzimidazoles with a peri-substituted naphthalene and a dimethylamino group at positions 1 and 2, respectively, was developed. We evaluated these compounds in the desymmetrization reaction of cis-tetrahydrophthalic anhydride with benzyl alcohol, as the nucleophilic sp2 imidazole nitrogen atom is able to catalyze the acyl-transfer reaction. The prepared benzimidazoles demonstrated catalytic activity and showed that their axial chirality impacts stereoselectivity.

References provided by Crossref.org

000      
00000naa a2200000 a 4500
001      
bmc25008241
003      
CZ-PrNML
005      
20250422095619.0
007      
ta
008      
250408s2025 enk f 000 0|eng||
009      
AR
024    7_
$a 10.1039/d4ob02052a $2 doi
035    __
$a (PubMed)39930802
040    __
$a ABA008 $b cze $d ABA008 $e AACR2
041    0_
$a eng
044    __
$a enk
100    1_
$a Toman, Daniel $u Department of Organic Chemistry, Faculty of Science, Palacký University Olomouc, 17. listopadu 1192/12, 77900 Olomouc, Czech Republic. petr.cankar@upol.cz $1 https://orcid.org/0000000250503808
245    10
$a Axially chiral dimethylaminobenzimidazoles and their preliminary evaluation as acyl-transfer reagents / $c D. Toman, I. Nemec, O. Kurka, A. Přibylka, P. Cankař
520    9_
$a The synthesis of axially chiral benzimidazoles with a peri-substituted naphthalene and a dimethylamino group at positions 1 and 2, respectively, was developed. We evaluated these compounds in the desymmetrization reaction of cis-tetrahydrophthalic anhydride with benzyl alcohol, as the nucleophilic sp2 imidazole nitrogen atom is able to catalyze the acyl-transfer reaction. The prepared benzimidazoles demonstrated catalytic activity and showed that their axial chirality impacts stereoselectivity.
590    __
$a NEINDEXOVÁNO
655    _2
$a časopisecké články $7 D016428
700    1_
$a Nemec, Ivan $u Department of Inorganic Chemistry, Faculty of Science, Palacký University Olomouc, 17. listopadu 1192/12, 77900 Olomouc, Czech Republic $1 https://orcid.org/0000000332317849
700    1_
$a Kurka, Ondřej $u Department of Analytical Chemistry, Faculty of Science, Palacký University Olomouc, 17. listopadu 1192/12, 77900 Olomouc, Czech Republic $1 https://orcid.org/0000000225335750
700    1_
$a Přibylka, Adam $u Department of Organic Chemistry, Faculty of Science, Palacký University Olomouc, 17. listopadu 1192/12, 77900 Olomouc, Czech Republic. petr.cankar@upol.cz $1 https://orcid.org/0000000337015460
700    1_
$a Cankař, Petr $u Department of Organic Chemistry, Faculty of Science, Palacký University Olomouc, 17. listopadu 1192/12, 77900 Olomouc, Czech Republic. petr.cankar@upol.cz $1 https://orcid.org/0000000274346069
773    0_
$w MED00007088 $t Organic & biomolecular chemistry $x 1477-0539 $g Roč. 23, č. 11 (2025), s. 2672-2682
856    41
$u https://pubmed.ncbi.nlm.nih.gov/39930802 $y Pubmed
910    __
$a ABA008 $b sig $c sign $y - $z 0
990    __
$a 20250408 $b ABA008
991    __
$a 20250422095620 $b ABA008
999    __
$a ok $b bmc $g 2306312 $s 1245316
BAS    __
$a 3
BAS    __
$a PreBMC-PubMed-not-MEDLINE
BMC    __
$a 2025 $b 23 $c 11 $d 2672-2682 $e 20250312 $i 1477-0539 $m Organic & biomolecular chemistry $n Org Biomol Chem $x MED00007088
LZP    __
$a Pubmed-20250408

Find record

Citation metrics

Archiving options