Aqueous/Nonaqueous DBU Mixtures: Versatile Switching Media for Chemoselective Aldol, Baylis-Hillman, and Aldol Condensation Reactions.

ABSTRACT: Isophorone is a relatively small molecule with several neighboring reacting sites, making it susceptible to various competing reactions with aldehydes, including aldol, Baylis-Hillman (BH), aldol condensation, and Michael addition reactions. In the present work, we have designed a switchable 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed procedure, where the reaction of isophorone with aldehydes is guided chemoselectively toward either aldol, BH, or aldol condensation reactions, depending on the use of water and/or heat. This controllable divergency likely stems from the ability to tune the dual nucleophilicity/basicity characters of the DBU/H₂O medium. In other words, the nucleophilicity of DBU plays a crucial role in directing the process toward the formation of the BH add

SUBMITTER: Akbarzadeh E 

PROVIDER: S-EPMC12820351 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature