Diisopinocampheylborane Trifluoromethanesulfonate-Mediated Aldol Reactions Using an Aldehyde and an Amide

Author

Camille Parker, Union College - Schenectady, NYFollow

Date of Award

6-2022

Document Type

Open Access

Degree Name

Bachelor of Science

Department

Chemistry

First Advisor

Lee Pedzisa

Keywords

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

Abstract

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.

Recommended Citation

Parker, Camille, "Diisopinocampheylborane Trifluoromethanesulfonate-Mediated Aldol Reactions Using an Aldehyde and an Amide" (2022). Honors Theses. 2622.
https://digitalworks.union.edu/theses/2622