Event: The Maryanoff Research Symposium
Date: 09/25/2017
Type: Oral Presentation (Powerpoint)
Title: Transition Metal-Catalyzed Reactions of Siloxy-Tethered 1,6 and 1,7-Enynes
Abstract:
The Pauson-Khand Reaction is important because this is one method to synthesize cyclopentanones which are readily found in the structure of a lot of natural products. This reaction can either be done inter- or intramolecular, though we focus on intramolecular as this will give us better stereoselectivity because the alkyne and alkene would be tethered together, therefore, reducing the chances that they can flip and have a different confirmation. The starting material needed to be synthesized as it was not cheap to buy from private companies. We wanted to see if we could synthesize it to reduce cost and make it more efficient. From this, we tested different R groups on the silicon atom. The two groups that were tested were phenol groups or isopropyl groups. It was seen that the isopropyl groups gave better yields, which was hypothesized because they are bulkier groups. So steric effects were a key effect that possibly helped improve yields. Further research needs to be done to see if other groups give better yields.
Date: 09/25/2017
Type: Oral Presentation (Powerpoint)
Title: Transition Metal-Catalyzed Reactions of Siloxy-Tethered 1,6 and 1,7-Enynes
Abstract:
The Pauson-Khand Reaction is important because this is one method to synthesize cyclopentanones which are readily found in the structure of a lot of natural products. This reaction can either be done inter- or intramolecular, though we focus on intramolecular as this will give us better stereoselectivity because the alkyne and alkene would be tethered together, therefore, reducing the chances that they can flip and have a different confirmation. The starting material needed to be synthesized as it was not cheap to buy from private companies. We wanted to see if we could synthesize it to reduce cost and make it more efficient. From this, we tested different R groups on the silicon atom. The two groups that were tested were phenol groups or isopropyl groups. It was seen that the isopropyl groups gave better yields, which was hypothesized because they are bulkier groups. So steric effects were a key effect that possibly helped improve yields. Further research needs to be done to see if other groups give better yields.