Date of Award


Document Type

Open Access

Degree Name

Bachelor of Science



First Advisor

Lee Pedzisa


Aldol, Organic chemistry, aldehyde, amide, small molecule, synthesis


Aldol reactions are one of the most powerful reactions in organic chemistry because of the formation of new carbon-carbon bonds. A downside of aldol reactions is that they generate a mix of stereoisomers, therefore a lot of work has gone into developing methods that selectively favor a certain stereoisomer. We report an enatio and diastereoselective diisopinocampheylborane trifluoromethanesulfonate ((Ipc)2BOTf) mediated aldol reaction with an amide and an aldehyde. Traditionally, (Ipc)2BOTf-mediated reactions were not applied to amides, except with the use of strong bases. Here we developed a (Ipc)2BOTf aldol reaction of amides using mild bases (iPr2NEt). Our lab was able to achieve an enantioselective and diastereoselective reaction, with an enantiomeric excess (ee) and diastereomeric ratio (d.r.) of up to >95% and >19:1, respectively for aliphatic aldehydes. We also expanded the scope of this reaction to include aromatic aldehydes and protected alcohol aldehydes.



Rights Statement

In Copyright - Educational Use Permitted.