Aldol reactions are one of the most powerful reactions in organic chemistry because of the formation of new carbon-carbon bonds. A downfall 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. Using a diisopinocampheylborane trifluoromethanesulfonate ((Ipc)2BOTf) mediated aldol reaction with an amide and propionaldehyde. 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 amine bases. Our lab was able to achieve an enantioselective and diastereoselective reaction, the product had an enantiomeric excess (ee) and diastereomeric ratio (d.r.) of &gt;95% and &gt;19:1, respectively. In the coming months, we plan to expand the scope of this research and apply it to the synthesis of small molecules.

Diisopinocampheylborane trifluoromethanesulfonate-mediated aldol reactions using an aldehyde and an amide

ACS Spring 2022

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