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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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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.
Selection Rules: Photochemical Activation
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to...
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Sharpless Epoxidation02:57

Sharpless Epoxidation

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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Enantioselective Photocatalysis Using a Privileged Al-Salen Complex.

Julia Soika1, Carina Onneken1, Tobias Morack1

  • 1Institute for Organic Chemistry, University of Münster, Corrensstraße 36, 48149 Münster, Germany.

Accounts of Chemical Research
|April 30, 2025
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Summary
This summary is machine-generated.

Aluminum-salen (Al-salen) catalysts, traditionally used in ground-state reactions, are now shown to be effective photocatalysts. Light activation enables new synthetic pathways for creating optically enriched molecules via deracemization and photocyclization.

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Area of Science:

  • Catalysis
  • Photochemistry
  • Organic Synthesis

Background:

  • Enantioselective catalysts are crucial for synthesizing chiral molecules.
  • Achieving high efficiency in excited-state catalysis remains a challenge.
  • Aluminum-salen (Al-salen) complexes show promise due to their photophysical properties.

Purpose of the Study:

  • To explore the potential of Al-salen complexes as photocatalysts.
  • To develop new structure-activation guidelines for excited-state catalysis.
  • To demonstrate Al-salen's utility in deracemization and photocyclization reactions.

Main Methods:

  • Utilized commercial Al-salen complexes for photochemical transformations.
  • Employed single electron transfer (SET) for deracemization of cyclopropyl ketones.
  • Applied energy transfer (EnT) catalysis for enantioselective photocyclization of acrylanilides.
  • Combined experimental and computational approaches for mechanistic studies.

Main Results:

  • Achieved efficient deracemization of cyclopropyl ketones (up to 98:2 e.r.) via a C(sp3)-C(sp3) bond cleavage/cyclization pathway.
  • Facilitated enantioselective photocyclization of acrylanilides to diverse heterocycles (up to quantitative yield and 96:4 e.r.).
  • Demonstrated Al-salen as a versatile chiral operator in distinct photochemical reactions.

Conclusions:

  • Light activation significantly expands the reactivity of Al-salen catalysts beyond ground-state applications.
  • Photochemical strategies overcome limitations of thermochemically challenging reactions.
  • This approach accelerates the discovery of chiral functional molecules.