Charge Relocation with Bogdan Brutiu Enables Stereodivergent 1,3-Difunctionalization of Alkenes

Stereodivergent 1,3-Difunctionalization of Alkenes by Charge Relocation with Bogdan Brutiu

Introduction:

The Stereodivergent 1,3-Difunctionalization of Alkenes by Charge Relocation is a powerful synthetic method that has been developed by Bogdan Brutiu. This method allows for the selective introduction of two different functional groups at the 1 and 3 positions of alkenes in a stereoselective manner. This tutorial will provide a step-by-step guide on how to perform this reaction using HTML tags.

Step 1: Setting up the Reactants

To start the reaction, you will need an alkene substrate, a suitable oxidant, and a nucleophile. In this tutorial, we will use ethylene as our alkene substrate, mCPBA as the oxidant, and any desired nucleophile. To represent these reactants in the HTML code, we can use the following tags:

<alkene>ethylene</alkene>
<oxidant>mCPBA</oxidant>
<nucleophile>desired nucleophile</nucleophile>

Step 2: Initiating the Reaction

The Stereodivergent 1,3-Difunctionalization of Alkenes by Charge Relocation reaction is initiated by the formation of an oxonium intermediate. This intermediate is formed by the attack of the oxidant on the alkene substrate. To represent this step in the HTML code, we can use the following tags:

<reaction>
<alkene>ethylene</alkene> + <oxidant>mCPBA</oxidant> -> oxonium intermediate
</reaction>

Step 3: Charge Relocation

Once the oxonium intermediate is formed, the charge is then relocated to the neighboring carbon atom, resulting in the formation of a carbocation intermediate. This step is crucial for the subsequent selective addition of the nucleophile at the 1 and 3 positions of the alkene. To represent this step in the HTML code, we can use the following tags:

<reaction>
oxonium intermediate -> carbocation intermediate
</reaction>

Step 4: Nucleophilic Addition

Finally, the nucleophile will selectively add to the 1 and 3 positions of the alkene to give the desired product. This step is highly stereoselective, allowing for the formation of different stereoisomers depending on the substituents present on the nucleophile. To represent this step in the HTML code, we can use the following tags:

<reaction>
carbocation intermediate + <nucleophile>desired nucleophile</nucleophile> -> desired product
</reaction>

Conclusion:

In conclusion, the Stereodivergent 1,3-Difunctionalization of Alkenes by Charge Relocation is a powerful synthetic method that allows for the selective introduction of two different functional groups at the 1 and 3 positions of alkenes in a stereoselective manner. By following the steps outlined in this tutorial, you can successfully perform this reaction using HTML tags.