A kinetic resolution of a diol via etherification catalyzed by a chiral phosphoric acid was developed and applied in the concise total synthesis of (+)-sacidumlignan D, the antipode of natural sacidumlignan D. A zinc-mediated crotylation of a diarylketone and subsequent lactonization quickly established the carbon framework of this class of tetrahydrofuran lignans.

A rapid synthetic route toward (±)-Bakuchiol is presented in 29% overall yield. After the sole all-carbon quaternary carbon center is created via allylboration of 2-aryl acetaldehyde, a "Pot-Economy" approach including mesylation, elimination, and desilylation was realized in the presence of ^tBuOK under ambient temperature to provide (±)-Bakuchiol.

To clarify the binding mechanisms and driving forces for the unique ability of pillar[5]arenes to recognize neutral molecules, the complexation of a series of nitrogen heterocycle substituted 1,4-butylene guests with pillar[5]arenes was studied. Guests molecules that have similar structures exhibit remarkably different association constants, and multiple weak C–H···N interactions between the alkyl groups of the pillar[5]arenes and the outer nitrogen atoms of the heterocycles of the guests are the dominant driving forces for complexation.

A concise synthesis of racemic Tapentadol and its stereoisomers was presented. The key step was a TiCl₄·THF₂-catalzyed aza-Belluš-Claisen rearrangement to create two vicinal tertiary carbon stereogenic centers. The subsequent reduction of amide and hydrogenation of alkene delivered Tapentadol and its stereoisomers. The current approach offers a practical synthetic route to access this class of pharmaceutically significant molecules.

A practical one-pot protocol for the synthesis of 2,5-disubstituted oxazoles from 1-aryl-2-nitroethanones was reported. In the presence of iron/AcOH in acetonitrile, the reaction of 1-aryl-2-nitroethanones with trimethyl orthoacetate or trimethyl orthobenzoate delivered the corresponding 2,5-disubstituted oxazoles in moderate to good yields.

Multicomponent cycloadditions with readily available isocyanides, allenoates, and isatylidene malononitriles are disclosed. This reaction, which does not require the aid of any catalyst, allows the efficient syntheses of spirocyclic oxindoles with excellent regioselectivity. Reactions with ethyl 2,3-butadienoate and various structurally diverse α- and γ-substituted allenoates are also fully explored. Remarkably, we have shown that the usual three-component process can be further developed into an unprecedented four-component cycloaddition in the presence of water, which provides a new strategy to access highly unusual tricyclic oxindoles. From a synthetic point of view, this protocol is very interesting considering the high level of complexity reached in one step. The mechanism is thought to proceed by a triple Michael/cyclization process by using allenoate as a three carbon atom component (3 C). Furthermore, multicomponent reaction with γ-substituted allenoate also results in a very interesting conversion. In such cases, the unusual cleavage of the “CC” double bond of isatylidene malononitrile and one of the “CC” double bonds of allenoate is always observed.

The intermolecular [2+2+1] multicomponent cycloadditions from readily available allenoates, dual activated olefins and isocyanides catalyzed by silver hexafluoroantimonate were studied. This protocol allowed the syntheses of highly functionalized five-membered carbocycles with exclusive regioselectivity and stereoselectivity in an efficient and atom-economical manner.

A simple and efficient protocol for CuI-catalyzed oxidative homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted 1,3-diynes was reported. The reaction can be carried out in the open air, using NaOAc as a base in the absence of any other additives. A variety of terminal alkynes were converted to the corresponding 1.3-diynes in good to excellent yields without any side product formation. Copyright © 2010 John Wiley & Sons, Ltd.

A novel approach for the synthesis of functionalized 1,5-benzodiazepine is described. The protocol is triggered by a tandem conjugated addition/cyclization process from the readily available starting materials 1,2-phenylenediamine and ethyl propiolate. The products have secondary amino and ester groups, and a β-enamino ester, which can serve in further functionalizations to produce molecular diversity.

The environmentally benign, regio- and stereoselective synthesis of functionalized tertiary amine 3 from acetates of Baylis-Hillman adducts with the aliphatic primary amines in the absence of any solvent and catalysts was reported.

A facile synthesis of N-substituted imidazole and benzotriazole derivatives from Baylis-Hillman bromides with imidazole and benzotriazole at room temperature was reported. In view of the simple operation, mild reaction conditions, good to excellent yields, good regio- and stereoselectivity, the present method exhibited its superiority.