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Enantioselective Organocatalytic Conjugate Addition of Malonates to β,β-Disubstituted β-Trifluoromethyl Enones under High Pressure

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide The first enantioselective Michael addition of malonates to acyclic β,β-disubstituted enones has been developed. Sterically hindered β-trifluoromethyl α,β-unsaturated 2-acyl thiazoles and benzothiazoles were found to be the most reactive groups of enones in the reaction catalyzed by bifunctional tertiary amine–thioureas (2–5 mol %). However, application of hyperbaric conditions (8–10 kbar) was required. The adducts containing quaternary stereogenic centers with a CF 3 group were obtained in high yields (vs <1% at 1 bar) with enantiomeric excesses up to 95%.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c00065

Authors: Alicja J. Połosak, Michał P. Głowacki, Piotr Kwiatkowski

Institution: University of Warsaw

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Narodowe Centrum Nauki