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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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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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Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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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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Copper-catalyzed asymmetric C(sp

Rupeng Qi1,2, Qiao Chen1, Liangyu Liu3

  • 1School of Pharmacy, Lanzhou University, 730000, Lanzhou, China.

Nature Communications
|June 6, 2023
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Summary
This summary is machine-generated.

This study introduces a new copper-catalyzed method for asymmetric cyanoalkylation, enabling the modification of peptides and amino acids. This advances peptide synthesis and drug discovery with high selectivity.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Alkylnitriles are crucial in various fields due to their electronic and structural properties.
  • Incorporating cyanoalkyl groups into amino acids and peptides offers potential for imaging and therapeutics.

Purpose of the Study:

  • To develop a copper-catalyzed asymmetric cyanoalkylation of C(sp3)-H bonds.
  • To enable the modification of amino acids and peptides with cyanoalkyl groups for potential applications.

Main Methods:

  • Copper-catalyzed asymmetric cyanoalkylation reaction.
  • Coupling of glycine derivatives with cycloalkanone oxime esters.
  • Late-stage modification of peptides.

Main Results:

  • High enantioselectivities achieved in the coupling of glycine derivatives and cycloalkanone oxime esters.
  • Successful late-stage modification of peptides with good yields and excellent stereoselectivities.
  • Mechanistic insights revealing the role of the copper complex in reduction and stereocontrol.

Conclusions:

  • The developed method provides an efficient route for synthesizing cyanoalkylated amino acids and peptides.
  • This approach is valuable for modern peptide synthesis and drug discovery.
  • The copper catalyst plays a dual role in mediating reduction and controlling stereoselectivity.