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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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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.1K
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...
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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Enantioselective Multifunctionalization with Rh Carbynoids.

Yu Qian1, Jie Tang1, Xiaoyu Zhou2

  • 1Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, China.

Journal of the American Chemical Society
|November 22, 2023
PubMed
Summary
This summary is machine-generated.

This study introduces the first asymmetric trifunctionalization using rhodium carbynoids. This novel method efficiently creates complex molecules by forming three new bonds in a single step, yielding diverse beta-amino esters with high enantioselectivity.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Multifunctionalization is key for efficient synthesis of complex molecules.
  • Reactions with metal carbynoids showing carbene/carbocation behavior are limited.
  • Developing enantioselective versions of these reactions is challenging.

Purpose of the Study:

  • To present the first asymmetric trifunctionalization reaction using rhodium carbynoids.
  • To demonstrate a novel strategy for constructing complex molecular scaffolds.
  • To achieve high yields and enantioselectivity in the synthesis of beta-amino esters.

Main Methods:

  • Utilizing rhodium carbynoids for trifunctionalization.
  • Employing a strategy involving the formation of two distinct carbene ylides.
  • Trapping one ylide with an imine to form three new bonds.

Main Results:

  • Successful development of the first asymmetric trifunctionalization with rhodium carbynoids.
  • Demonstration of the carbynoid precursor reacting with two nucleophiles and one electrophile.
  • High yields and exceptional enantioselectivity in the synthesis of diverse beta-amino esters.

Conclusions:

  • This work establishes a new benchmark in asymmetric catalysis.
  • The developed method offers a powerful tool for divergent synthesis.
  • The strategy enables efficient and enantioselective construction of valuable beta-amino ester scaffolds.