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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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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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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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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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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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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.
9.8K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

11.3K
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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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.6K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.8K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.8K

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Switchable regioselectivity in amine-catalysed asymmetric cycloadditions.

Zhi Zhou1, Zhou-Xiang Wang1, Yuan-Chun Zhou1

  • 1Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, China.

Nature Chemistry
|May 25, 2017
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Summary

This study introduces novel, switchable cycloaddition reactions using cinchona-derived primary amines. These reactions enable the creation of diverse small molecules with high regio- and stereoselectivity, valuable for drug discovery.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Asymmetric Catalysis

Background:

  • Small-molecule libraries with structural and stereogenic diversity are crucial for drug discovery.
  • Developing switchable cycloaddition reactions with controlled regioselectivity and high stereoselectivity is a significant challenge in organic synthesis.

Purpose of the Study:

  • To develop versatile cycloaddition reactions of α'-alkylidene-2-cyclopentenones using cinchona-derived primary amine catalysts.
  • To achieve switchable regioselectivity and high stereoselectivity in intermolecular cycloaddition reactions for generating diverse chiral molecules.

Main Methods:

  • Utilized cinchona-derived primary amines as catalysts for asymmetric cycloadditions.
  • Employed in situ generation of formal 4-aminofulvenes for [6+2] cycloadditions with 3-olefinic (7-aza)oxindoles.
  • Developed a dual catalysis system with amines and thiols for α,γ-regioselective [4+2] cycloadditions with maleimides.

Main Results:

  • Achieved an asymmetric γ,β'-regioselective intermolecular [6+2] cycloaddition with high regio- and stereoselectivity.
  • Disclosed a β,γ-regioselective [2+2] cycloaddition with maleimides, yielding fused cyclobutanes.
  • Uncovered an unprecedented α,γ-regioselective [4+2] cycloaddition using dual amine and thiol catalysis.
  • Demonstrated excellent regio- and stereoselectivity across all reported cycloaddition reactions.

Conclusions:

  • The developed catalytic systems provide an attractive and versatile protocol for constructing complex chiral architectures.
  • These methods significantly enhance structural and stereogenic diversity in small-molecule libraries, advancing drug discovery efforts.
  • The ability to switch reaction pathways and achieve high selectivity offers powerful tools for synthetic organic chemistry.