2015
DOI: 10.1002/ange.201506793
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Regulating Molecular Recognition with C‐Shaped Strips Attained by Chirality‐Assisted Synthesis

Abstract: Chirality-assisted synthesis (CAS) is ag eneral approach to control the shapes of large molecular strips. CASisbased on enantiomerically pure building blocks that are designed to strictly couple in as ingle geometric orientation. Fully shape-persistent structures can thus be created, even in the form of linear chains.W ithC AS,s elective recognition between large host and guest molecules can reliably be designed de novo.T od emonstrate this concept, three C-shaped strips that can embrace ap illar[5]arene macro… Show more

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Cited by 20 publications
(13 citation statements)
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“…This process can be thought of as a chirality-directed macrocyclization strategy. 57,58 Rac-5, which has one protonated aminomethyl group and one carboxylic group, is very reactive and cannot be easily chirally-resolved by chiral HPLC. Compound rac-4 is more stable and was thus selected and subjected to chiral HPLC for enantioseparation.…”
Section: Synthesis and Characterization Of Chiral Naphthotubesmentioning
confidence: 99%
“…This process can be thought of as a chirality-directed macrocyclization strategy. 57,58 Rac-5, which has one protonated aminomethyl group and one carboxylic group, is very reactive and cannot be easily chirally-resolved by chiral HPLC. Compound rac-4 is more stable and was thus selected and subjected to chiral HPLC for enantioseparation.…”
Section: Synthesis and Characterization Of Chiral Naphthotubesmentioning
confidence: 99%
“…After purification, a colorless powder was obtained (mp > 410 °C, decomposition starts at 350−360 °C). (+)-(M)- 8b,8b,12b,12dtetrahydrodibenzo[2,3:4,5]pentaleno [1,6-ab]indene-2,6,10-triol ((+)-(M)-1). In a pressure tube, tris(camphanic acid ester) (+)-(M,S)-3 (354 mg, 0.35 mmol, 1.0 equiv) was added to a solution of KOH (559 mg, 9.96 mmol, 28.5 equiv) in methanol (35 mL).…”
Section: ■ Experimental Sectionmentioning
confidence: 99%
“…[α] 578 21 = +173. 7,8b,8b,12b,3:4,5]pentaleno[1,6-ab]indene-2,6,10-triol ((±)-4). To a suspension of tris(phenol) (±)-1 (117 mg, 0.25 mmol, 1.0 equiv) in trifluoroacetic acid (2.3 mL) in a screw-capped reaction tube (8 mL content) was added Niodosuccinimide (202 mg, 0.90 mmol, 3.6 equiv) in small portions under stirring.…”
Section: ■ Experimental Sectionmentioning
confidence: 99%
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“…Because of the electron- rich cavity of pillar[n]arenes, neutral molecules are the preferred guests because multiple CH/π interactions can form to stabilize the host−guest complex (Figure 1b). 22,23 The cavity size of pillar[5]arenes is ca. 4.7 Å, which accommodates linear molecules.…”
Section: Introductionmentioning
confidence: 99%