A new format for the Castagnoli-Cushman reaction of structurally diverse dicarboxylic acids, amines, and aldehydes in the presence of acetic anhydride as dehydrating agent is described. The reaction is distinctly amenable to parallel format: the combinatorial array of 180 reactions delivered 157 products of >85% purity without chromatographic purification (of this number, 143 compounds had >94% purity). The new method offers a convenient preparation of the skeletally and peripherally diverse, lead- and druglike β- and β-lactam carboxylic acids with high diastereoselectivity in combinatorial fashion.

Original languageEnglish
Pages (from-to)702-707
Number of pages6
JournalACS Combinatorial Science
Volume19
Issue number11
DOIs
StatePublished - 13 Nov 2017

    Scopus subject areas

  • Chemistry(all)

    Research areas

  • Castagnoli-Cushman reaction, cyclodehydration, diversity-oriented synthesis, multicomponent reactions, phase separation, Schiff bases, skeletal diversity

ID: 34634267