Yaneirys Cruz
2007 Participant
Carbonyl-Ylide Cycloadditions on Carbohydrate Templates
Reactions involving Ylides have become a powerful tool in organic synthesis over the years; ylides were first identified in 1953 by George Wittig. An ylide consists of a carbanion bonded to a positively charged heteroatom. The work of this project examines the (3+2)-cycloaddition reaction of carbonyl ylides with sugar templates mannose and arabinose. This is a reaction that has not been studied extensively. Carbonyl ylides are 1,3-dipolar compounds having the structure shown below with a distribution of charge over three atoms. The stereochemistry of the carbonyl ylide is inherited from the starting material because of how the product is formed in the transition state.
The products we'll be getting will consist of complex five member ring heterocyclic compounds with four new stereocenters and are expected to be optically active. We are in the preliminary stages of the work.