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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Cyclotriveratrylene-BINOL-Based Host Compounds: Synthesis, Absolute Configuration Assignment, and Recognition

Sara Lefevre1, Alexandre Héloin1, Delphine Pitrat1

  • 1Laboratoire de Chimie, École Normale Supérieure de Lyon , CNRS, UCBL 46, Allée d'Italie, F-69364 Lyon, France.

The Journal of Organic Chemistry
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Summary
This summary is machine-generated.

New chiral host compounds were synthesized for carbohydrate recognition. These cyclotriveratrylene-based molecules show preferential binding for mannose over glucose, demonstrating potential as chiral sensors.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Chiral Recognition

Background:

  • Development of novel host compounds is crucial for selective molecular recognition.
  • Cyclotriveratrylene (CTV) scaffolds offer unique structural properties for host-guest chemistry.
  • Chiral recognition of carbohydrates remains a significant challenge in chemistry.

Purpose of the Study:

  • To synthesize novel enantiomerically and diastereomerically pure host compounds.
  • To investigate the carbohydrate binding properties of these new CTV-based hosts.
  • To evaluate their potential as chiral sensors for sugar derivatives.

Main Methods:

  • Enantioselective and diastereoselective synthesis of CTV-binaphthol conjugates.
  • Absolute configuration assignment using chemical correlation.
  • Measurement of epimerization energy barriers.
  • Carbohydrate binding studies using selectivity assays.

Main Results:

  • Successfully synthesized pure CTV-host compounds.
  • Determined absolute configurations and measured epimerization barriers.
  • Observed preferential binding of mannose over glucose.
  • Achieved good diastereoselectivities in carbohydrate recognition (up to 1:10).

Conclusions:

  • Open-shell CTV-based host compounds are effective in recognizing carbohydrate derivatives.
  • These compounds exhibit unprecedented selectivity for sugar recognition.
  • The developed host molecules show promise as versatile chiral sensors.