Organic: MacMillan Organocatalyast Mechanism

In summary, the individual is struggling to understand the mechanism of a reaction catalyzed by MacMillan Generation 1 and 2 organocatalysts. They have read a paper on MacMillan, but found it difficult to comprehend. They attempted to draw the reaction without using the catalyst, but their professor informed them that it would not work. They are seeking help in understanding the role of the catalyst and how it makes the reaction enantioselective.
  • #1
uchicago2012
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Homework Statement


I'm trying to figure out the mechanism for a reaction catalyzed by MacMillan Generation 1 and 2 organocatalysts. Not going so well. I don't understand what role the organocatalyst plays in the reaction. I read a paper about MacMillan and I think it was saying that the catalysts worked by forming an imminium ion, but the entire thing was way over my head, so I'm not so sure about that. I drew the reaction without even using the catalyst but my prof said that reaction wouldn't go. I don't really understand how the mechanism works, what the catalyst does to make the reaction 'go,' and how the catalyst makes the reaction enantioselective. Apparently it's a magical substance, I don't know. Can anyone help me with the mechanism? I would feel a great deal better if I knew what these catalysts were running around doing in the reaction.

The Attempt at a Solution


Gen1Genral: General Reaction with Generation One organocatalyst
Gen2General: General reaction with Generation Two organocatalyst
WrongMech: the first mechanism I tried that doesn't have the catalysts and is wrong
NewMech: the newest one I tried that is also probably wrong, seeing as I am stuck (on post under this one)
aldrichchemica: MacMillan paper, in case anyone else can actually understand it (on post under this one)
 

Attachments

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  • Gen2General.png
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  • WrongMech.jpg
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  • #2
NewMech: the newest one I tried that is also probably wrong, seeing as I am stuck
aldrichchemica: MacMillan paper, in case anyone else can actually understand it
 

Attachments

  • NewMech.jpg
    NewMech.jpg
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  • aldrichimica.pdf
    1.1 MB · Views: 285

1. What is organic: MacMillan organocatalyst mechanism?

The MacMillan organocatalyst mechanism is a type of catalytic reaction in organic chemistry that involves the use of small organic molecules as catalysts. These catalysts can facilitate a wide range of reactions, including carbon-carbon bond formations, asymmetric reactions, and more. They offer a more environmentally-friendly and cost-effective alternative to traditional metal-based catalysts.

2. How does the MacMillan organocatalyst mechanism work?

The exact mechanism of the MacMillan organocatalyst is still being studied and understood, but it is believed to involve the formation of an iminium ion intermediate, which then reacts with the substrate to form the desired product. The catalyst itself is not consumed in the reaction and can be reused multiple times.

3. What are the advantages of using the MacMillan organocatalyst mechanism?

The use of organic molecules as catalysts offers several advantages, such as high efficiency, mild reaction conditions, and a wide range of applications. These catalysts also have minimal environmental impact and are often more cost-effective than traditional metal-based catalysts.

4. What are some common applications of the MacMillan organocatalyst mechanism?

The MacMillan organocatalyst mechanism has been used in a variety of reactions, including aldol reactions, Michael additions, and Diels-Alder reactions. It has also been applied in the synthesis of natural products, pharmaceuticals, and other important organic compounds.

5. Are there any limitations to the MacMillan organocatalyst mechanism?

Like any chemical reaction, the MacMillan organocatalyst mechanism has its limitations. Some reactions may not be suitable for this type of catalysis, and the catalysts may not work well under certain conditions. Additionally, the synthesis of these catalysts can be challenging and may require specialized equipment and techniques.

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