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Related Concept Videos

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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.
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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 stereochemistry.

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Published on: November 9, 2019

Catalytic diastereoselective petasis reactions.

Giovanni Muncipinto1, Philip N Moquist, Stuart L Schreiber

  • 1Broad Institute of Harvard and MIT, Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.

Angewandte Chemie (International Ed. in English)
|July 14, 2011
PubMed
Summary

Researchers developed the first diastereoselective Petasis reaction using chiral biphenols. This multicomponent reaction efficiently synthesizes pure syn and anti β-amino alcohols from boronates, aldehydes, and amines.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Published on: April 4, 2014

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The Petasis reaction is a versatile multicomponent reaction.
  • Achieving diastereoselectivity in Petasis reactions remains a challenge.
  • Chiral catalysts are crucial for asymmetric synthesis.

Purpose of the Study:

  • To develop the first diastereoselective Petasis reaction.
  • To synthesize syn and anti β-amino alcohols with high purity.
  • To utilize chiral biphenols as catalysts.

Main Methods:

  • Employed a multicomponent approach involving boronates, α-hydroxy aldehydes, and amines.
  • Utilized chiral biphenols as catalysts for the Petasis reaction.
  • Optimized reaction conditions to achieve high diastereoselectivity.

Main Results:

  • Successfully developed the first diastereoselective Petasis reaction.
  • Achieved the synthesis of both syn and anti β-amino alcohols in pure form.
  • Demonstrated the efficacy of chiral biphenol catalysts in controlling stereochemistry.

Conclusions:

  • Chiral biphenol-catalyzed Petasis reactions provide a novel route to diastereomerically pure β-amino alcohols.
  • This methodology offers a significant advancement in asymmetric synthesis.
  • The developed reaction expands the synthetic utility of multicomponent reactions.