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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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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 form a...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

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Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.       
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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
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A Catalytic Asymmetric Hydrolactonization.

Rajat Maji1, Santanu Ghosh1, Oleg Grossmann1

  • 1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.

Journal of the American Chemical Society
|April 12, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed a catalytic asymmetric hydrolactonization method using a novel imidodiphosphorimidate (IDPi) Brønsted acid catalyst. This breakthrough addresses a long-standing challenge in organic synthesis, enabling efficient and scalable reactions.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Electrophile-induced lactonization reactions are crucial in organic synthesis.
  • Catalytic asymmetric hydrolactonization of olefinic carboxylic acids remains a significant challenge.
  • Previous methods have limitations in scope and efficiency.

Purpose of the Study:

  • To develop a novel catalytic asymmetric hydrolactonization method.
  • To address the long-standing challenge of archetypical hydrolactonization.
  • To provide a scalable and versatile synthetic route.

Main Methods:

  • Utilized a confined imidodiphosphorimidate (IDPi) Brønsted acid catalyst.
  • Employed olefinic carboxylic acids as substrates.
  • Conducted detailed mechanistic studies using physicochemical and DFT analyses.

Main Results:

  • Successfully achieved catalytic asymmetric hydrolactonization.
  • Demonstrated operational simplicity, scalability, and broad substrate compatibility.
  • Showcased the method's utility through the synthesis of (-)-boivinianin A and (+)-gossonorol.

Conclusions:

  • The developed IDPi Brønsted acid catalyst effectively enables asymmetric hydrolactonization.
  • This method offers a practical and efficient approach to synthesizing complex molecules.
  • Mechanistic insights provide a deeper understanding of the reaction's enantioselectivity.