4.4 Article

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

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TETRAHEDRON
卷 65, 期 2, 页码 536-539

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.103

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  1. CONACyT [48356-Q]
  2. PAPIIT-UNAM [N226706-3]

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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. (C) 2008 Elsevier Ltd. All rights reserved.

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