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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.

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Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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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...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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Catalytic asymmetric transacetalization.

Ilija Corić¹, Sreekumar Vellalath, Benjamin List

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

Journal of the American Chemical Society

|June 10, 2010

Summary

This summary is machine-generated.

A new catalytic method allows for enantioselective transacetalization using TRIP, a chiral phosphoric acid. This reaction provides a novel route for the asymmetric synthesis of acetals, creating a single stereogenic center.

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Published on: June 21, 2017

Area of Science:

Organic Chemistry
Asymmetric Synthesis

Background:

Transacetalization is a key reaction in organic synthesis.
Developing enantioselective methods for acetal formation is crucial for accessing chiral molecules.

Purpose of the Study:

To develop a catalytic enantioselective transacetalization reaction.
To utilize chiral phosphoric acids as catalysts for this transformation.

Main Methods:

Employing TRIP (a chiral phosphoric acid) as a catalyst.
Reacting O,O-acetals under catalytic conditions.

Main Results:

TRIP demonstrated high efficiency and enantioselectivity in transacetalization.
The reaction successfully produced acetals with a single stereogenic center.

Conclusions:

A novel catalytic enantioselective transacetalization has been achieved.
Chiral phosphoric acid TRIP is an effective catalyst for asymmetric acetal synthesis.