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 in:Tetrahedron 2009-01, Vol.65 (2), p.536-539
Main Authors: Priego, Jaime, Ortíz-Nava, Claudia, Carrillo-Morales, Manuel, López-Munguía, Agustín, Escalante, Jaime, Castillo, Edmundo
Format: Article
Language:English
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
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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