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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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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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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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Prochirality

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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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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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A General Catalytic Asymmetric Prins Cyclization.

Luping Liu1, Philip S J Kaib1, Aurélien Tap1

  • 1Max-Planck-Institut für Kohlenforschung , Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.

Journal of the American Chemical Society
|August 23, 2016
PubMed
Summary
This summary is machine-generated.

New imino-imidodiphosphate (iIDP) Brønsted acids enable asymmetric Prins cyclization. This efficient catalytic method yields functionalized tetrahydropyrans, valuable for synthesizing fragrances like rose oxide.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • The Prins cyclization is a key reaction for forming tetrahydropyran structures.
  • Developing efficient and enantioselective methods for this transformation remains a significant challenge in organic synthesis.

Purpose of the Study:

  • To introduce a novel class of highly acidic confined imino-imidodiphosphate (iIDP) Brønsted acids.
  • To utilize these catalysts for the asymmetric Prins cyclization of aldehydes.

Main Methods:

  • Employing confined imino-imidodiphosphate (iIDP) Brønsted acids as catalysts.
  • Reacting aliphatic and aromatic aldehydes under catalytic conditions to promote Prins cyclization.
  • Analyzing reaction products for yield, regio-, and enantioselectivity.

Main Results:

  • Achieved good to excellent yields of diverse functionalized 4-methylenetetrahydropyrans.
  • Demonstrated good to excellent regio- and enantioselectivities in the cyclization products.
  • Successfully applied the iIDP catalysts to the synthesis of fragrance compounds, including rose oxide and doremox.

Conclusions:

  • The developed iIDP Brønsted acids represent a new class of effective catalysts for asymmetric Prins cyclization.
  • This methodology offers an efficient and scalable enantioselective route to valuable tetrahydropyran derivatives.
  • The catalytic system is applicable to the synthesis of important fragrance molecules.