Date of Award
Bachelor of Science
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.
Parker, Camille, "Diisopinocampheylborane Trifluoromethanesulfonate-Mediated Aldol Reactions Using an Aldehyde and an Amide" (2022). Honors Theses. 2622.