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Diversity-oriented synthesis of β-lactams was achieved via Ugi/Michael reaction cascades under mild conditions. The intramolecular hydrogen bonding between the heteroatom from an aldehyde component and the amide NH group controls the chemoselectivity of the Michael reaction versus the aza-Michael reaction. DFT calculation was performed to clarify the mechanism, chemo-selectivity and diastereoselectivity of this work. This one-pot protocol offers a straightforward method to build a diversified β-lactam library for drug discovery.
This article was published in the following journal.
Name: Organic & biomolecular chemistry
A bifunctional squaramide-catalyzed asymmetric cascade aza-Michael/Michael addition reaction for the synthesis of chiral spirothiazolidinone tetrahydroquinolines with three contiguous stereocenters ha...
Enantioselective synthesis of tricyclic δ-lactones with three contiguous stereocenters has been demonstrated by the N-heterocyclic carbene (NHC)-catalyzed functionalization of benzylic C(sp)-H bonds....
The first copper-catalyzed highly chemo-, regio-, diastereo-, and enantioselective Kinugasa/Michael domino reaction for the desymmetrization of prochiral cyclohexadienones is described. In the presenc...
Total stereo-selective Michael Addition of N- and S- nucleophiles to a D-erythrosyl 1,5-lactone derivative. Experimental and theoretical studies devoted to the synthesis of 2,6-dideoxy-4-functionalized-D-ribono-hexono-1,4-lactone.
The synthesis of a 1,5-lactone 2,4-O-alkylidene-D-erythrose derivative was found to be a highly stereoselective template in Michael addition trough the reaction of a D-erythrosyl 1,5-lactone derivativ...
Detailed kinetic analysis for the Cu(I)-catalyzed Kinugasa reaction forming β-lactams has revealed an anomalous overall zero-order reaction profile, due to opposing positive and negative orders in ni...
Concentrations and effects of β-Lactams in critically ill children are unpredictable and the risk of under-exposure may be associated with poor clinical outcomes. In addition, between-sub...
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LACTAMS forming compounds with a ring size of approximately 1-3 dozen atoms.
Cyclic AMIDES formed from aminocarboxylic acids by the elimination of water. Lactims are the enol forms of lactams.
A reaction characterized by a violet color upon the addition of copper sulfate to all compounds with two amide or peptide bonds linked directly or through an intermediate carbon atom. Used in the detection and estimation of proteins and peptides having more than two amino acids.
An ATP-dependent enzyme that catalyzes the addition of ADP to alpha-D-glucose 1-phosphate to form ADP-glucose and diphosphate. The reaction is the rate-limiting reaction in prokaryotic GLYCOGEN and plant STARCH biosynthesis.
An early local inflammatory reaction to insult or injury that consists of fever, an increase in inflammatory humoral factors, and an increased synthesis by hepatocytes of a number of proteins or glycoproteins usually found in the plasma.
Clinical Approvals Clinical Trials Drug Approvals Drug Delivery Drug Discovery Generics Drugs Prescription Drugs In the fields of medicine, biotechnology and pharmacology, drug discovery is the process by which drugs are dis...