Synthesis of an inherently chiral O,O′-bridged thiacalix[4]crowncarboxylic acid and its application to a chiral solvating agent

Narumi, Fumitaka; Hattori, Tetsutaro; Matsumura, Nobuji; Onodera, Toru; Katagiri, Hiroshi; Kabuto, Chizuko; Kameyama, Hiroshi; Miyano, Sotaro

doi:10.1016/j.tet.2004.06.074

Cited by 53 publications

(5 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We [7][8][9][10][11] have recently reported an efficient approach to the synthesis of enantiopure inherently chiral calix [4] crowns by introduction of a chiral auxiliary and then separation of subsequent diastereomers via preparative TLC or even column chromatography on silica gel, and further found [10] that a tetra-O-alkylated inherently chiral fluorescent calix [4]crown-6 in the partial cone conformation could show considerable enantioselective recognition capability towards chiral leucinol. Some other groups also reported the similar compounds [12][13][14] . Accordingly, enantiopure inherently chiral calix [5]crowns could be obtained [11] .…”

Section: Introductionmentioning

confidence: 69%

Enantiopure inherently chiral calix[4]arene derivatives containing quinolin-2-yl-methanol moiety: Synthesis and application in the catalytic asymmetric addition of diethylzinc to benzaldehyde

Miao

Huang

et al. 2009

Sci. China Ser. B-Chem.

View full text Add to dashboard Cite

A series of novel N,O-type chiral ligands derived from enantiopure inherently chiral calix[4]arenes containing quinolin-2-yl-methanol moiety in the cone or partial-cone conformation have been synthesized and characterized. Moreover, they have been applied to the catalytic asymmetric addition of diethylzinc to benzaldehyde, which represents the first example that the inherently chiral calixarene can be used as the chiral ligands for the catalytic asymmetric synthesis.inherently chiral calixarenes, synthesis, N,O-type chiral ligand, asymmetric catalysis, diethylzinc

show abstract

Section: Introductionmentioning

confidence: 69%

Enantiopure inherently chiral calix[4]arene derivatives containing quinolin-2-yl-methanol moiety: Synthesis and application in the catalytic asymmetric addition of diethylzinc to benzaldehyde

Miao

Huang

et al. 2009

Sci. China Ser. B-Chem.

View full text Add to dashboard Cite

show abstract

“…In most cases thiacalixarenes can be modified in analogous ways to calixarenes, e.g., for preparation of 29. 46 Chiral recognition properties of 29 towards amines and amino acid esters were assessed. Diastereomeric salts, stable at the NMR timescale, were formed in most cases allowing for effective enantiomer discrimination by chemical shifts.…”

Section: Heterocalixarenesmentioning

confidence: 99%

Inherently chiral concave molecules—from synthesis to applications

2010

View full text Add to dashboard Cite

This tutorial review covers the recent development in the synthesis and application of molecules and finite assemblies that are chiral owing to their curvature. A modified definition of inherent chirality is provided. Various classes of chiral concave molecules are presented including salphen complexes, cyclic amides, derivatives of sumanene, trioxatricornan or subphthalocyanine, cyclotriveratrylenes, homooxacalix[3]arenes, calixarenes, resorcinarenes, phthalocyanines, corannulenes and cavitands. Some of these bowl shaped compounds exhibit high inversion barriers, comparable with the stability of classical carbon chirality centres, while the others (e.g. hydrogen bonded assemblies) can only be detected by NMR. This review is focused on practical aspects of synthesis, resolution and applications in chiral recognition and asymmetric synthesis.

show abstract

“…Receptors based on such compounds can recognize and bind optical antipodes of chiral “guest”. They are promising as ligands for metallocomplex catalysts [6,7] and organocatalysts [8] in asymmetric synthesis, enantioselective sensors, [9–11] chiral stationary phases in chromatography, [12,13] chiral shift reagents for NMR studies, [14,15] etc. Therefore, the development of convenient and preparative methods for the synthesis of inherently chiral calix[4] is an urgent task of organic and supramolecular chemistry.…”

Section: Introductionmentioning

confidence: 99%

25‐Propyloxy‐26,27‐dibenzoyloxy‐calix[4]arene as Precursor for the Synthesis of Inherently Chiral Calixarenes

et al. 2021

View full text Add to dashboard Cite

This paper shows that 25‐propyloxy‐26,27‐dibenzoyloxy‐calix[4]arene can be a convenient precursor for the formation of inherently chiral configuration on the calixarene platform. The methods for sequential regioselective debenzoylation and electrophilic substitution on the upper rim were developed. The inherently chiral calix[4]renes with two and three different functional groups on the upper rim were synthesized.

show abstract

Synthesis of an inherently chiral O,O′-bridged thiacalix[4]crowncarboxylic acid and its application to a chiral solvating agent

Cited by 53 publications

References 54 publications

Enantiopure inherently chiral calix[4]arene derivatives containing quinolin-2-yl-methanol moiety: Synthesis and application in the catalytic asymmetric addition of diethylzinc to benzaldehyde

Enantiopure inherently chiral calix[4]arene derivatives containing quinolin-2-yl-methanol moiety: Synthesis and application in the catalytic asymmetric addition of diethylzinc to benzaldehyde

Inherently chiral concave molecules—from synthesis to applications

25‐Propyloxy‐26,27‐dibenzoyloxy‐calix[4]arene as Precursor for the Synthesis of Inherently Chiral Calixarenes

Contact Info

Product

Resources

About