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Literature DB >> 15826169

Electrostatic manipulation of enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate within gamma-cyclodextrin cavity through chemical modification. inverted product distribution and enhanced enantioselectivity.

Abstract

In the enantiodifferentiating supramolecular photocyclodimerization of 2-anthracenecarboxylate using gamma-cyclodextrin with a dicationic side chain, a dramatic switching of the product selectivity and a significant enhancement of the enantiomeric excess were achieved by introducing a flexible dicationic sidearm to native gamma-cyclodextrin and also by lowering the temperature and solvent polarity.

Entities: Chemical

Year: 2005 PMID： 15826169 DOI： 10.1021/ja050704e

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

7 in total

1. Synthesis of a Disulfonated Derivative of Cucurbit[7]uril and Investigations of its Ability to Solubilize Insoluble Drugs.

Authors: Elizabeth L Robinson; Peter Y Zavalij; Lyle Isaacs
Journal: Supramol Chem Date: 2015-05-01 Impact factor: 1.688

2. DFT study of the per-6-amino-β-cyclodextrin as catalyst in synthesis of 2-aryl-2,3-dihydro-4-quinolones.

Authors: Yali Wan; Xueye Wang; Na Liu
Journal: J Mol Model Date: 2014-08-20 Impact factor: 1.810

Review 3. Synthesis of cyclodextrin derivatives for enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate.

Authors: Xueqin Wei; Jiecheng Ji; Yongxin Nie; Liangjian Tang; Ming Rao; Xiaoqian Wang; Wanhua Wu; Dan Su; Zhihui Zhong; Cheng Yang
Journal: Nat Protoc Date: 2022-08-31 Impact factor: 17.021

Electrostatic manipulation of enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate within gamma-cyclodextrin cavity through chemical modification. inverted product distribution and enhanced enantioselectivity.

1. Synthesis of a Disulfonated Derivative of Cucurbit[7]uril and Investigations of its Ability to Solubilize Insoluble Drugs.

2. DFT study of the per-6-amino-β-cyclodextrin as catalyst in synthesis of 2-aryl-2,3-dihydro-4-quinolones.

Review 3. Synthesis of cyclodextrin derivatives for enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate.

Review 4. Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis.

5. Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene.

6. Supramolecular FRET photocyclodimerization of anthracenecarboxylate with naphthalene-capped γ-cyclodextrin.

7. Enantioselective Hydrolysis of Amino Acid Esters Promoted by Bis(β-cyclodextrin) Copper Complexes.