Journal
TETRAHEDRON
Volume 66, Issue 17, Pages 3187-3194Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.02.085
Keywords
NADH; beta-Lactams; DFT calculations; Enantioselective reduction
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Funding
- Ministerio de Educacion y Ciencia (MEC, Spain) [CTQ2006-13891/BQU]
- UPV-EHU and Gobierno Vasco [IE-08/225]
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Conformationally restricted NADH peptidomimetics 4a-e, characterized by the presence of a (1,4-dihydronicotinamide)-(beta-lactam) moiety, have been synthesized and used to study the Mg2+ cation-promoted asymmetric reduction of alkyl aroylformates in acetonitrile. Increasing the bulkiness of peripheral substituents at the nitrogen atom of the beta-lactam ring, at the 1,4-dihydronicotinamide moiety, or at the aroylformate ester group, was found to cause weak but clearly detectable variations of the enantiomeric excess of the reaction. A rational for these observations was consistent with a chelated NADH/Mg2+/ArCOCO2R3 ternary complex model, according to DFT calculations computed at a B3LYP/631G(sic) theory level. (C) 2010 Elsevier Ltd. All tights reserved.
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