Alpha-imino anions are generated under neutral reaction conditions via a Pd-mediated decarboxylation of allyl diphenylglycinate imines with concomitant formation pi-allylpalladium species. The resulting delocalized anion can attack the pi-allyl-Pd(II) species or be intercepted by aldehydes to afford homoallylic amines protected 1,2-amino alcohols, respectively.

The Pd-catalyzed decarboxylative allylation of α-(diphenylmethylene)imino esters (1) or allyl diphenylglycinate imines (2) is an efficient method to construct new C(sp(3))-C(sp(3)) bonds. detailed mechanism this reaction was studied by theoretical calculations [ONIOM(B3LYP/LANL2DZ+p:PM6)] combined with experimental observations. overall catalytic cycle found consist three steps: oxidative addition, decarboxylation, and reductive allylation. addition 1 [(dba)Pd(PPh(3))(2)] (dba =...

A palladium-catalyzed asymmetric decarboxylative allylic alkylation of allyl 2,2-diphenylglycinate imines using (S,S)-f-binaphane as a chiral supporting ligand has been developed. This transformation allows for generation and enantioselective allylation nonenolate α-imino (2-azaallyl anions) to afford α-aryl homoallylic imines.

Interception of the Pd-catalyzed decarboxylative allylation allyl diphenylglycinate imines with appropriately functionalized Michael acceptors, followed by Heck cyclization, allows for efficient construction relatively complex organoamine frameworks in one reaction vessel. The initial intercepted is remarkably insensitive toward solvent and catalyst, typically proceeding under ambient conditions.

Antibiotic resistance is a significant problem and compounded by the ability of many pathogenic bacteria to form biofilms. A library N-substituted derivatives previously reported 2-aminoimidazole/triazole (2-AIT) biofilm modulator was constructed via α-bromoketone cyclization with 1,3-bis(tert-butoxycarbonyl)guanidine, followed selective substitution. Several compounds exhibited inhibit formation three strong forming strains methicillin resistant Staphylococcus aureus (MRSA). Additionally,...

Condensation between the tetrabutylammonium salt of 2,2-diphenylglycine and aldehydes results in a decarboxylative Erlenmeyer reaction, affording 1,2-diaryl-2-iminoalcohols as mixture diastereomers good yields. The diastereomeric ratio shifts over time, with anti diastereomer syn oxazolidine tautomer serving kinetic thermodynamic products, respectively. Addition Lewis acids can catalyze rates reaction product equilibration. highlight stereochemical promiscuity presence Brønsted bases.

Abstract A library of 4,5‐disubstituted 2‐aminoimidazole triazole amide (2‐AITA) conjugates has been successfully assembled. Upon biological screening, this class small molecules was discovered as enhanced biofilm regulators through non‐microbicidal mechanisms against methicillin‐resistant Staphylococcus aureus (MRSA) and multidrug‐resistant Acinetobacter baumannii (MDRAB), with active concentrations in the low micromolar range. The also subjected to synergism resensitization studies...

Information literacy is of paramount importance to any successful research program. techniques and skills should be infused throughout a student's undergraduate curriculum rather than being the focus single course. To this end, we have created several courses, beginning in first year, where students review current scientific literature, design experiments, collect analyze data, disseminate their findings both written oral formats. At completion sequence greater understanding all aspects...

Commercially utilized parabens are employed for their antimicrobial properties, but a weak binding to the estrogen receptor alpha (ERα) may lead breast cancer in some applications. Modification of paraben scaffold should allow disconnection these observed properties. Toward this goal, various 3,5-substituted were synthesized and assessed properties against S. aureus as well competitive ERα. The minimum inhibitory concentration assay confirmed retention activity many derivatives, while all...

A broadly applicable semester-long course-based undergraduate research experience (CURE)-inspired organic II laboratory course was developed from an engaging story supported by the current literature surrounding paraben use in consumer products. The project involves synthesis of brominated parabens followed investigation into structure–activity relationship between ester lipophilicity and antimicrobial properties. synthetic route for mirrors sequence reactions topics typically covered a...

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Abstract using (S,S)‐f‐binaphane (BPF) as chiral catalyst ligand

Abstract Starting from tetrabutylammonium 2,2‐diphenylglycinate and (hetero)aromatic aldehydes the reaction provides a mixture of syn‐ anti‐2‐iminoalcohols, syn‐isomer which exists in an equilibrium with its oxazolidine tautomer.

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