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Related Concept Videos

α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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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...
4.2K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.1K
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...
4.1K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.8K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.8K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

8.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
8.0K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.9K
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...
9.9K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

5.4K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Enantioselective α-Amination Enabled by a BINAM-Derived Phase-Transfer Catalyst.

H M Nelson1, J S Patel1, H P Shunatona1

  • 1Department of Chemistry, University of California, Berkeley, California 94720, United States.

Chemical Science
|December 9, 2014
PubMed
Summary

Chiral phase-transfer catalysis enables highly enantioselective alpha-amination of carbonyl compounds using aryldiazonium salts. BINAM-derived phosphoric acids are key to achieving high stereoselectivity in this valuable synthetic transformation.

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Area of Science:

  • Organic Chemistry
  • Asymmetric Catalysis

Background:

  • Enantioselective synthesis of alpha-amino carbonyl compounds is crucial for pharmaceuticals.
  • Developing efficient catalytic methods for C-N bond formation remains a challenge.

Purpose of the Study:

  • To develop a highly enantioselective alpha-amination of carbonyl compounds.
  • To explore the use of chiral anion phase-transfer catalysis for this transformation.

Main Methods:

  • Utilized chiral anion phase-transfer of aryldiazonium cations.
  • Employed BINAM-derived phosphoric acids as catalysts.
  • Applied the method to indanone- and benzosuberone-derived substrates.

Main Results:

  • Achieved highly enantioselective alpha-amination of carbonyl compounds.
  • Demonstrated broad substrate scope including indanone and benzosuberone derivatives.
  • Confirmed the critical role of BINAM-derived phosphoric acids in high enantioselectivity.

Conclusions:

  • Chiral anion phase-transfer is an effective strategy for enantioselective alpha-amination.
  • The developed method provides access to valuable alpha-amino acid derivatives.
  • This approach offers a new route for synthesizing chiral amines.