Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate: New Developments

Synthesis DOI: 10.1055/s-0040-1708017 The earlier described reaction of homophthalic anhydrides with aromatic ketones and ammonium acetate was tested for cyclic ketones (yielding spirocyclic motifs) and aliphatic aldehydes. In contrast to previous findings, the reaction was found to require no catalyst at all and to be applicable, in the non-catalyzed format, to these new carbonyl substrates as well as aromatic ketones. The reaction typically proceeds with high diastereoselectivity; if not, the initial diastereomeric mixture can be quantitatively equilibrated into a single, trans-diastereomer on treatment with aqueous base. [...] © Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - April 15, 2020 Category: Chemistry Authors: Safrygin, Alexander Bakulina, Olga Dar ’in, Dmitry Krasavin, Mikhail Tags: paper Source Type: research