[reaction: see text] A high-yielding method is described for the rapid synthesis of very hindered cyclohexenes by the Diels-Alder reaction of hindered silyloxy dienes and dienophiles using the mixed Lewis acid catalyst system (AlBr(3)/AlMe(3)). Thus, reaction of the hindered diene 4 with various substituted enones gave good yields of the expected cycloadducts even though both partners are quite sterically hindered.
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http://dx.doi.org/10.1021/ol050361p | DOI Listing |
Org Biomol Chem
January 2025
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology (ECUST), Shanghai 200237, China.
A highly efficient base-controlled synthesis of -β-trifluoromethyl-substituted 2-benzo[]imidazole-2-thiones and 2-fluoro-4-benzo[4,5]imidazo[2,1-][1,3]thiazines hydroamination or defluorinative cyclizations of α-(trifluoromethyl)styrenes with 2-mercaptobenzimidazole was developed.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Univ Rennes, CNRS, ISCR - UMR 6226, F-35000 Rennes, France.
A straightforward and highly diastereoselective synthesis of -4-hydroxypiperidines is presented. This method allows access to C2 and C4 substituted piperidines, bearing a tetrasubstituted carbon stereocenter at C4. -Disubstituted homoallylic amines and ketoaldehydes as carbonyl partners have been rarely used in aza-Prins cyclizations, expanding the scope of this reaction.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
State Key Laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
The ever-increasing demand in chemical biology and medicinal research requires the development of new synthetic methods for the rapid construction of libraries of heterocycles from simple raw materials. In this context, the utilization of primary amines or HO as the simple - or -sources in the assembly of a heterocyclic ring skeleton is highly desirable from the viewpoint of atom- and step-economy. Herein, we describe a highly efficient three-component reaction of diazo, allylic diacetates, and commercially available anilines (or HO) to access structurally diverse pyrrolidine and tetrahydrofuran derivatives.
View Article and Find Full Text PDFJ Med Chem
January 2025
Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Science, Southern Medical University, Guangzhou 510515, P. R. China.
CDK2 and CDK9 play pivotal roles in cell cycle progression and gene transcription, respectively, making them promising targets for cancer treatment. Herein, we discovered a series of -(substituted thiazol-2-yl)--(4-substituted phenyl)pyrimidine-2,4-diamines as highly potent CDK2/9 dual inhibitors. Especially, compound significantly inhibited CDK2 (IC = 0.
View Article and Find Full Text PDFAcc Chem Res
January 2025
Laboratory for Chemistry and Life Science (CLS), Institute of Integrated Research, Institute of Science Tokyo, 4259 Nagatsuta, Midori-ku, Yokohama 226-8501, Japan.
ConspectusThe design of properties and functions of molecular assemblies requires not only a proper choice of building blocks but also control over their packing arrangements. A highly versatile unit in this context is a particular type of triptycene with substituents at the 1,8,13-positions, called tripodal triptycene, which offers predictable molecular packing and multiple functionalization sites, both at the opposite 4,5,16- or 10 (bridgehead)-positions. These triptycene building blocks are capable of two-dimensional (2D) nested hexagonal packing, leading to the formation of 2D sheets, which undergo one-dimensional (1D) stacking into well-defined "2D+1D" structures.
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