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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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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Nitriles to Amines: LiAlH4 Reduction00:55

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Preparation of Amines: Reduction of Amides and Nitriles01:13

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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
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Generality-Driven Catalyst Development: A Universal Catalyst for Enantioselective Nitroalkene Reduction.

Zihang Deng1, Melanie A Padalino1, Julius E L Jan1

  • 1Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, United States.

Journal of the American Chemical Society
|January 4, 2024
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Summary
This summary is machine-generated.

A new organocatalyst offers broad applicability in asymmetric catalysis, overcoming a major hurdle in developing new therapeutic compounds. This discovery provides high selectivity and generality for diverse small molecules.

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Area of Science:

  • Organic chemistry
  • Asymmetric catalysis

Background:

  • The selectivity-generality paradox hinders the application of new asymmetric catalysis methods to diverse small molecules.
  • This limitation is particularly impactful in therapeutic development, where rapid access to structurally varied compounds is crucial.

Purpose of the Study:

  • To develop a versatile catalytic system that bridges the gap between high selectivity and broad substrate scope in asymmetric catalysis.
  • To apply this system to the synthesis of diverse peptidomimetics.

Main Methods:

  • Development of a novel organocatalyst designed for generality-driven enantioselective catalysis.
  • Application of the organocatalyst to the preparation of a range of peptidomimetic structures.

Main Results:

  • A single new organocatalyst demonstrated high enantioselectivity and broad substrate generality.
  • The catalyst's performance rivals that of combined metal and organocatalyst systems.
  • This represents a significant advancement, breaking a long-standing paradigm in organocatalysis.

Conclusions:

  • The new organocatalyst provides a powerful scaffold for enantioselective reduction.
  • The catalyst's behavior suggests a novel mechanism involving recognition of a nitroethylene minimal catalaphile.
  • This work facilitates the efficient synthesis of diverse small molecules for drug discovery.