Axially Chiral Sulfonic Acids for Bronsted Acid Catalysis: 8-Benzoimidazolylnaphthalene-1-sulfonic Acids and Their Derivatives

被引：1

作者：

Tomanova, Monika ^{[1
]}

Vankova, Iva ^{[1
]}

Toman, Daniel ^{[1
]}

Pribylka, Adam ^{[1
]}

Nemec, Ivan ^{[2
]}

Cankar, Petr ^{[1
]}

机构：

[1] Palacky Univ, Fac Sci, Dept Organ Chem, Olomouc 77146, Czech Republic

[2] Palacky Univ, Fac Sci, Dept Inorgan Chem, Olomouc 77146, Czech Republic

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 13期

关键词：

RESOLUTION;

D O I：

10.1021/acs.joc.3c00818

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new type of axiallychiral sulfonic acid was developed.The synthesisis based on cheap commercially available materials and a practicalmethod for optical resolution via diastereomeric salt formation, whichcan provide both enantiomers. Eleven benzoimidazolylnaphthalenesulfonicacids were prepared and four of them were isolated as pure and stableatropisomers. Moreover, several of these sulfonic acids were transformedinto triflyl imides to further expand the range of dissociation constants.

引用

页码：9265 / 9276

页数：12

共 50 条

[21] Arylamine salts as derivatives for identifying aromatic sulfonic acids
Dermer, OC
Dermer, VH
JOURNAL OF ORGANIC CHEMISTRY, 1942, 7 (06): : 581 - 586
[22] SPECIFIC EFFECTS IN ACID CATALYSIS BY POLYMERIC SULFONIC ACIDS IN HYDROLYSIS OF SOME CARBOXYLIC ESTERS
YOSHIKAWA, S
KIM, OK
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1966, 39 (07) : 1515 - +
[23] Design, synthesis and applications of new families of chiral sulfonic acids
Jakubec, Pavol
Muratore, Michael E.
Aillaud, Isabelle
Thompson, Amber L.
Dixon, Darren J.
TETRAHEDRON-ASYMMETRY, 2015, 26 (5-6) : 251 - 261
[24] SULFONIC-ACIDS - L-HOMOCYSTEINESULFONIC ACID
HAYWARD, MA
CAMPBELL, EB
GRIFFITH, OW
METHODS IN ENZYMOLOGY, 1987, 143 : 279 - 281
[25] SULFONIC ACIDS OF FLUORESCEIN .1. CONDENSATION OF SULFOPHTHALIC ACIDS WITH RESORCINOL
IOFFE, IS
DEVYATOVA, NI
ROSKULYAK, LA
JOURNAL OF GENERAL CHEMISTRY USSR, 1962, 32 (07): : 2081 - &
[26] SPECIFIC EFFECTS IN ACID CATALYSIS BY POLYMERIC SULFONIC ACIDS IN HYDROLYSIS OF AMINO ESTER AND RELATED COMPOUNDS
YOSHIKAWA, S
KIM, OK
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1966, 39 (08) : 1729 - +
[27] SYNTHESIS OF 1-METHYLAMINO-4-CHLOROANTHRAQUINONE-5-AND-8-SULFONIC ACIDS
RODINA, NA
KURDYUMO.TN
JOURNAL OF GENERAL CHEMISTRY USSR, 1964, 34 (04): : 1314 - &
[28] THERMAL AND PHOTOLYTIC STABILITIES OF PERFLUOROALKANE SULFONIC-ACIDS AND THEIR DERIVATIVES
GERMAIN, A
OUDRHIRI, M
BRUNEL, D
COMMEYRAS, A
JOURNAL OF FLUORINE CHEMISTRY, 1980, 16 (06) : 627 - 627
[29] DL CAMPHOR 3-SULFONIC ACID AND OTHER KETO ALPHA-SULFONIC ACIDS
CREMLYN, RJ
WU, L
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1988, 39 (3-4): : 165 - 171
[30] SYNTHESIS OF 5-NITROFLUORANTHEN-4-SULFONIC AND 5-AMINOFLUORANTHEN-4-SULFONIC ACIDS AND THEIR DERIVATIVES
BURMISTR.SI
ZINCHENK.VM
ZHURNAL ORGANICHESKOI KHIMII, 1970, 6 (02): : 375 - &

← 1 2 3 4 5 →