Bridging Chiral <i>de‐tert</i>‐Butylcalix[4]arenes: Diastereomeric Crystallization‐Based Optical Resolution and Determination of Absolute Configuration

Liu, Wen-Shan; He, Di; Ma, Hao; Weng, Xiu‐Fang; Ren, Shuhang; Liu, Xiong; Tang, Sing Hai; Ma, Shengming; Liu, Junmin; Li, Shaoyong

doi:10.1002/slct.201802804

Cited by 8 publications

(2 citation statements)

References 10 publications

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“…The effects of solvent, temperature, and time were explored by Li et al in the diastereomeric crystallization of bridging chiral detert-butylcalix [4]arenes by using (1S)-(+)-10-camphorsulfonyl chloride as chiral auxiliary. 887 As shown in Figure 72, diverse outcomes are possible upon crystallization of achiral and chiral molecules. 888 Upon a crystallization process without the involvement of a chiral resolving agent, the racemic mixture may provide (a) a racemic compound; (b) a pseudoracemate, namely, a racemic solid solution; or (c) a racemic conglomerate through the formation of an equimolar mechanical mixture of crystals, each formed by homochiral molecules.…”

Section: Enantioselective Adsorption and Permeationmentioning

confidence: 99%

“…On this basis, the racemic resolution and formation of bis(brucinium)- N -(3-nitrobenzoyl)- l -aspartate hydrate MeOH solvate was found related to three-point recognition of the anions by brucinium self-assembly. The effects of solvent, temperature, and time were explored by Li et al in the diastereomeric crystallization of bridging chiral de - tert -butylcalix[4]arenes by using (1 S )-(+)-10-camphorsulfonyl chloride as chiral auxiliary …”

Section: Trends In Enantioselective Recognition In Natural and Synthe...mentioning

confidence: 99%

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Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

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Section: Enantioselective Adsorption and Permeationmentioning

confidence: 99%

Section: Trends In Enantioselective Recognition In Natural and Synthe...mentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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Design and Synthesis of Bridging Chiral p–t‐Butylcalix[4]arene Tetrahydroisoquinolines and Their Application in Henry Reaction as Chiral Organocatalysts

Weng

et al. 2019

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A pair of bridging chiral p‐t‐butylcalix[4]arenes (2a and 2b) (were) synthesized from 1 through homologous anionic ortho‐Fries rearrangement, and optically resolved with (1S)‐(+)‐10‐camphorsulfonyl chloride as chiral auxiliary. Bridging chiral p‐t‐butylcalix[4]arene tetrahydroisoquinolines (9a and 9b) as chiral organocatalysts for Henry reaction were designed and synthesized through the structural modification of 2a and 2b, respectively. Compared to the catalytic enantioselectivity of the unmodified tertiary amine (4b: ∼0% ee and 63% yield), those of the tetrahydroisoquinoline derivatives (9b: up to 13.4% ee and 96% yield) were distinctly enhanced. Although the increase magnitude of the catalytic ee is not remarkable, these catalytic results prove that the conformation inversion of calix[4]arene skeleton and the rotational freedom reduction of catalytic amine group indeed bring beneficial effects on the catalytic stereoselectivity.

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Synthesis of Bridging Chiral p–tert‐Butylcalix[4]arenes with One and Two Carbamoyl Bridge‐Substituents through Anionic Ortho‐Fries Rearrangement

Weng

Ren

et al. 2020

ChemistrySelect

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Bridging chiral p‐tert‐butylcalix[4]arenes (p‐t‐Bu‐BCC's) with different N‐substituted carbamoyl bridge‐substituents (N,N‐dimethylcarbamoyl, N,N‐diethylcarbamoyl and morpholinocarbonyl) were successfully prepared through anionic ortho‐Fries rearrangement from mono‐O‐carbamates of 1,3‐dipropyl‐p‐tert‐butylcalix[4]arene in 65–75% yield. In addition, p‐t‐Bu‐BCC with two N,N‐dimethylcarbamoyl bridge‐substituents was produced by this method from mono‐O‐carbamate of p‐t‐Bu‐BCC with one N,N‐dimethylcarbamoyl bridge‐substituent in 71% yield. However, the synthesis of p‐t‐Bu‐BCC with additional carbamoyl bridge‐substituents using this method could not be attempted, as the required rearrangement precursor failed to be synthesized. Finally, the racemic p‐t‐Bu‐BCC with morpholinocarbonyl bridge‐substituent was optically resolved into a pair of enantiomers, whose absolute configurations were determined through ROESY analysis and ECD comparison.

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Bridging Chiral de‐tert‐Butylcalix[4]arenes: Diastereomeric Crystallization‐Based Optical Resolution and Determination of Absolute Configuration

Cited by 8 publications

References 10 publications

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Design and Synthesis of Bridging Chiral p–t‐Butylcalix[4]arene Tetrahydroisoquinolines and Their Application in Henry Reaction as Chiral Organocatalysts

Synthesis of Bridging Chiral p–tert‐Butylcalix[4]arenes with One and Two Carbamoyl Bridge‐Substituents through Anionic Ortho‐Fries Rearrangement

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