Lake Superior State University
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“LSSU gave me the educational and organizational tools to be able to succeed at those endeavors after college.”

Scott Shackleton '83

Former State House of Representatives

LSSU Outstanding Alumnus Award '05

Special Education: Learning Disabilities

 

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Asymmetric Synthesis Using Chiral Auxiliaries and Titanium Enolates

Michael Overbeek

Chiral auxiliary-mediated asymmetric aldol additions are an important method for asymmetric carbon-carbon bond formation. Dr. Daveid A. Evans from Harvard University has developed the use of a boron enolate to allow for specific stereochemistry, often called an ďEvanís Aldol Reactioní. The use of a titanium enolate, instead of a borony enolate, has been documented to create the opposite stereocenters when utilizing the Evanís Aldol methodology. This project describes an attempt to form an anti-Evans product with the addition of phenylacetaldehyde to R-(-)-4-Benzyl-3propionyl-2oxazolidinone. The use of an aldehyde substrate when utilizing a chiral titanium enolate has not been well documented in the literature.

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