Pseudoacids. II. 2-Acylbenzoic Acid Derivatives

Valente, E.; Martin, Samuel B.; Sullivan, L.D.

doi:10.1107/s0108768197012020

Cited by 8 publications

(5 citation statements)

References 23 publications

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“…[11] To perform preferential crystallization, it is a requirement that the materials crystallize as a conglomerate. [12] Recrystalli-zation of the other isoindolinones in a chloroform-hexane solution afforded prismatic crystals except in the case of 1 b. [12] Recrystalli-zation of the other isoindolinones in a chloroform-hexane solution afforded prismatic crystals except in the case of 1 b.…”

mentioning

confidence: 99%

Total Spontaneous Resolution by Deracemization of Isoindolinones

et al. 2012

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Separated: 3-hydroxy-3-phenylisoindolin-1-ones have been resolved by dynamic preferential crystallization. The compounds were effectively racemized through ring-opening and ring-closing reactions via achiral intermediates under basic conditions. Crystallization from a toluene solution containing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with stirring and evaporation of the solvent gave optically active crystals quantitatively with high ee values.

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confidence: 99%

Total Spontaneous Resolution by Deracemization of Isoindolinones

et al. 2012

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“…In the Cambridge Structural Database (CSD), there are seven crystal structures of compounds that maintain the same 2-benzoylbenzamide molecule as the core molecule, only by changing the composition of the groups bonded to the nitrogen atom [15,[39][40][41]. Here, these molecules will be mentioned by their CSD reference code as follow: anti-N-Benzyl-Nethyl-2-benzoylbenzamide (BERDUY) 15 , N,N-Dibenyl-2-benzoylbenzamide (BERDAY) [15], N-Morpholino-2-benzoylbenzamide (NOSYEZ) [40], N,N-Dimethyl-2-benzoylbenzamide (OBEXOI/OBEXOI01)] [35,39], N-Methyl-N-phenyl-2-benzoylbenzamide (OBEXUO) [39] and 2'-2-(benzenecarbonyl)benzene-1-carbonylspiroindene-2,1'-isoindole-1,3,3'(2'H)-trione (SONFUZ) [41]. Molecular structures and torsion angles are given in SI, Figure S4 and Table S1.…”

Section: Database Surveymentioning

confidence: 99%

The Polymorphism of 2-Benzoyl-N,N-diethylbenzamide

et al. 2021

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The crystal structures of two new polymorphs of 2-benzoyl-N,N-diethylbenzamide were obtained after recrystallization trials with different solvents. The new forms II and III were monoclinic and crystallized in the same space group with similar a, b and c lengths but different β angles. The forms had no conformation differences within themselves; however, the long-range packing (>two unit cells) was not isostructural. In comparison with the previously published crystal structure, form I, different conformations and packing arrangements were observed. The new form II was thermally characterized and stable at room temperature, when heated up to its melting point and when cooled to −170 °C. Additionally, once form II was re-heated, a fourth form is observed after a phase transition from the monoclinic to the orthorhombic crystal systems, form IV.

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“…21 However, up to now, there are still few reports on the chiral symmetry breaking resolution of enantiomers and newly reported systems can be summarized as axially chiral systems, 34,35,45 acids with a chiral stereogenic center at the α-position, 46-49 and isoindolinones. 50,51 The first example of resolution for axially chiral systems was reported by Pincock et al in 1970s (Scheme 3). 34 Although a series of works on the resolution of 1,1′-binaphthyl (3) have been carried out to present that the chiral resolution occurred, 34,35 a systematic investigation of 1,1′-binaphthyl was not carried out by Kondepudi until 1999 (Scheme 4).…”

Section: Racemate-to-homochiral Approach For Separation Of the Enanti...mentioning

confidence: 99%

“…The crystal structure of 13c was reported with the chiral space group P2 1 2 1 2 1 . 51 Recrystallization of the other isoindolinones in a chloroform-hexane solution afforded 13d and 13f in the chiral space group P2 1 2 1 2 1 . By controlling the rates of racemization and crystallization, the optimized conditions of the concentration of 13 and the catalyst for the resolution were set up.…”

Section: Racemate-to-homochiral Approach For Separation Of the Enanti...mentioning

confidence: 99%

The racemate-to-homochiral approach to crystal engineering via chiral symmetry breaking

Yan

Sun

et al. 2015

CrystEngComm

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CrystEngComm HIGHLIGHTGuangming Li et al.The racemate-to-homochiral approach to crystal engineering via chiral symmetry breaking VolumeThe racemate-to-homochiral approach is a method to transform or separate a racemic mixture into homochiral compounds. This protocol, if without an external chiral source, is categorized into chiral symmetry breaking. The resolution processes without chiral induction are highly important for the investigation of the origin of homochirality in life, pharmaceutical synthesis, the chemical industry and materials science. Besides the studies on the models and mechanisms used to explain the racemate-to-homochiral approach which may give the probable origin of homochirality in life, recent developments in this field have been plotted towards the separation of enantiomers for the synthesis of pharmaceuticals and chiral chemicals. Direct synthesis of chiral metal-organic framework (MOF) coordination polymers has been achieved as well. In this highlight, we will disclose the comparison of spontaneous resolution and chiral symmetry breaking resolution, and describe the evolution of models and mechanisms for chiral symmetry breaking resolution and its applications in enantiomer resolution and materials science.

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Pseudoacids. II. 2-Acylbenzoic Acid Derivatives

Cited by 8 publications

References 23 publications

Total Spontaneous Resolution by Deracemization of Isoindolinones

Total Spontaneous Resolution by Deracemization of Isoindolinones

The Polymorphism of 2-Benzoyl-N,N-diethylbenzamide

The racemate-to-homochiral approach to crystal engineering via chiral symmetry breaking

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