Gold/Chiral Amine Relay Catalysis Enables Asymmetric Synthesis of C2-Quaternary Indolin-3-ones.

A mild and effective strategy for the asymmetric synthesis of C2-quaternary indolin-3-ones from 2-alkynyl arylazides and ketones by gold/chiral amine relay catalysis is described. In this reaction, 2-alkynyl arylazides undergo gold-catalyzed cyclization, nucleophilic attack, and oxidation to form intermediate 2-phenyl-3H-indol-3-ones, followed by an l-proline-catalyzed asymmetric Mannich reaction with ketones, to afford corresponding products in satisfactory yields with excellent enantio- and diastereoselectivities.

Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3-Containing Spiro[pyrrolidin-3,2'-oxindole].

An asymmetric double oxidative [3 + 2] cycloaddition is reported. Oxidation of 3-((2,2,2-trifluoroethyl)amino)indolin-2-ones and ß-aryl-substituted aldehydes simultaneously and subsequent asymmetric cycloaddition in the presence of the chiral amino catalyst generated highly functionalized chiral CF3-containing spiro[pyrrolidin-3,2'-oxindole] with four contiguous stereocenters stereoselectively, which is characterized by directly constructing two C-C bonds from four C(sp3)-H bonds. This new method features mild conditions, broad substrate scope, and excellent functional group compatibility.

Gold-Catalyzed Cascade Reaction of 2-Alkynyl Aryl Azides with Enecarbamates for Direct Synthesis of α-(3-Indolyl)ketones.

α-(3-Indolyl)ketones are essential building blocks for the generation of biologically active molecules. We described a new method for the direct assembly of α-(3-indolyl)ketones through the cascade reaction of 2-alkynyl aryl azides with enecarbamates, in which the in situ generated α-imino gold carbene intermediate was trapped by enecarbamate to achieve umpolung reactivity of indole at the 3-position.

Access to 3-Sulfonamidoquinolines by Gold-Catalyzed Cyclization of 1-(2'-Azidoaryl)propargylsulfonamides through 1,2-N Migration.

We describe a gold-catalyzed cyclization of 1-(2'-azidoaryl)propargylsulfonamides for the synthesis of 3-sulfonamidoquinolines, featuring a rare and highly selective 1,2-N migration. The key α-imino gold carbene intermediate is generated through an intramolecular nucleophilic attack of the azide group to the Au-activated triple bonds in a 6-endo-dig manner.

Free Vibration Analysis of a Graphene-Reinforced Porous Composite Plate with Different Boundary Conditions.

Plates are commonly used in many engineering disciplines, including aerospace. With the continuous improvement in the capacity of high value-added airplanes, large transport aircrafts, and fighter planes that have high strength, high toughness, and corrosion resistance have gradually become the development direction of airplane plate structure production and research. The strength and stability of metal plate structures can be improved by adding reinforced materials. This paper studies graphene platelets (GPLs) reinforced with a free vibration porous composite plate. The porous plate is constructed with a multi-layer model in a metal matrix containing uniform or non-uniformly distributed open-cell internal pores. Considering the random and directional arrangement of graphene platelets in the matrix, the elastic modulus of graphene composites was estimated using the Halpin-Tsai micromechanical model, and the vibration frequencies of graphene composite were calculated using the differential quadrature method. The effects of the total number of layers, GPL distribution pattern, porosity coefficient, GPL weight fraction, and boundary conditions on the free vibration frequency of GPLs reinforced porous composite plates are studied, and the accuracy of the conclusions are verified by the finite element software.

Generalized PID observer design for descriptor linear systems.

A type of generalized proportional-integral-derivative observers is proposed for descriptor linear systems. Based on a general parametric solution to a type of generalized Sylvester matrix equations, a parametric design approach for such observers is established. The proposed approach provides parameterizations for all the observer gain matrices, gives the parametric expression for the corresponding left eigenvector matrix of the observer system matrix, realizes the elimination of impulsive behaviors, and guarantees the regularity of the observer system. The design method can offer all the degrees of design freedom, which can be utilized to achieve various desired system specifications and performances. In addition, a numerical example is employed to show the design procedure and illustrate the effect of the presented approach.