Stereomodulating effect of remote groups on the NADH-mimetic reduction of alkyl aroylformates with 1,4-dihydronicotinamide-β-lactam amides
作者： Jesus M. Aizpurua , Claudio Palomo , Raluca M. Fratila , Pablo Ferrón , José I. Miranda
DOI: 10.1016/J.TET.2010.02.085
关键词:
摘要: Abstract Conformationally restricted NADH peptidomimetics 4a–e, characterized by the presence of a (1,4-dihydronicotinamide)-(β-lactam) moiety, have been synthesized and used to study Mg2+ cation-promoted asymmetric reduction alkyl aroylformates in acetonitrile. Increasing bulkiness peripheral substituents at nitrogen atom β-lactam ring, 1,4-dihydronicotinamide or aroylformate ester group, was found cause weak but clearly detectable variations enantiomeric excess reaction. A rational for these observations consistent with chelated NADH/Mg2+/ArCOCO2R3 ternary complex model, according DFT calculations computed B3LYP/6-31G∗ theory level.
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