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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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Chiral binary metal-organic frameworks for asymmetric sequential reactions.

Zijian Li1, Yan Liu, Qingchun Xia

  • 1School of Chemistry and Chemical Engineering and State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China. liuy@sjtu.edu.cn yongcui@sjtu.edu.cn.

Chemical Communications (Cambridge, England)
|November 3, 2017
PubMed
Summary

Chiral porous metal-organic frameworks (MOFs) were developed as efficient catalysts for sequential alkene epoxidation and epoxide ring-opening reactions, achieving high enantioselectivity up to 99%. These advanced materials offer precise control over catalytic processes.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Catalysis

Background:

  • Metal-organic frameworks (MOFs) are crystalline porous materials with tunable structures and properties.
  • Asymmetric catalysis is crucial for synthesizing enantiomerically pure compounds.
  • Sequential reactions offer efficient pathways for complex molecule synthesis.

Purpose of the Study:

  • To synthesize chiral porous MOFs with precisely arranged metallosalen active sites.
  • To investigate the catalytic performance of these MOFs in asymmetric sequential alkene epoxidation and epoxide ring-opening reactions.

Main Methods:

  • Synthesis of two chiral porous metal-organic frameworks (MOFs).
  • Characterization of the MOFs' structure and active site arrangement.
  • Evaluation of catalytic activity and enantioselectivity in sequential reactions.

Main Results:

  • The synthesized chiral MOFs demonstrated high efficiency as heterogeneous catalysts.
  • Enantioselectivity of up to 99% was achieved in the asymmetric sequential reactions.
  • Precise spatial arrangement of metallosalen active sites was confirmed.

Conclusions:

  • Chiral porous MOFs with tailored active sites are effective for asymmetric sequential catalysis.
  • These MOFs provide a promising platform for developing highly enantioselective catalytic processes.
  • The study highlights the potential of MOFs in advanced organic synthesis.