Solvent engineering: an effective tool to direct chemoselectivity in a lipase-catalyzed Michael addition

• Published in: Tetrahedron Vol. 65; no. 2; pp. 536 - 539
• Main Authors: Priego, Jaime, Ortíz-Nava, Claudia, Carrillo-Morales, Manuel, López-Munguía, Agustín, Escalante, Jaime, Castillo, Edmundo
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 10.01.2009; Elsevier
• Subjects: Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Chemistry; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; Kinetics and mechanisms; Methods. Procedures. Technologies; Organic chemistry; Reactivity and mechanisms; Michael addition; Catalytic reaction; Crotonic acid; Enzyme; Chemoselectivity; Polar solvent; Triacylglycerol lipase; Hydrophobic compound; Esterases; Selectivity; Carboxylic ester hydrolases; Enzymatic method; Aminolysis; Addition reaction; Hydrolases; Carboxamide; Polarity; Chemical synthesis; Structural analysis

A solvent engineering strategy was implemented in order to control the chemoselectivity in a lipase-catalyzed Michael addition reaction. This strategy was revealed as a high-effective tool for the selective synthesis of Michael adduct 3 or aminolysis product 4 from benzylamine 1 and methyl crotonate...