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

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...

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Bibliographic Details
Published inTetrahedron 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
LanguageEnglish
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
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Summary: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 2. Chemoselectivity of the enzymatic process was elucidated in terms of polarity of the medium, hence, adduct 3 was preferentially accumulated in hydrophobic medium, whereas in polar solvents the amide 4 was preferentially formed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.10.103