Convenient Access to Functionalized Vinylcyclopentenols from Alkynyloxiranes

Wang, Letian; Maddess, Matthew L.; Lautens, Mark

doi:10.1021/jo062107w

Cited by 29 publications

(3 citation statements)

References 22 publications

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“…This effect is of high practical importance since it offers a complementary method for activating already existing metathesis catalysts. [34] In addition, unlike freon and some aromatic hydrocarbons, FAHs do not seem to pose much environmental or biological risk. [35] FAHs can improve the efficiency of the initiation step of phosphine-containing Ru pre-catalysts, as was indicated by much faster decomposition of the Grubbs catalysts Gru-II in solutions containing FAH.…”

Section: Resultsmentioning

confidence: 99%

The Doping Effect of Fluorinated Aromatic Solvents on the Rate of Ruthenium‐Catalysed Olefin Metathesis

Samojłowicz

Bieniek

Pazio

et al. 2011

Chemistry A European J

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A study concerning the effect of using a fluorinated aromatic solvent as the medium for olefin metathesis reactions catalysed by ruthenium complexes bearing N‐heterocyclic carbene ligands is presented. The use of fluorinated aromatic hydrocarbons (FAH) as solvents for olefin metathesis reactions catalysed by standard commercially available ruthenium pre‐catalysts allows substantially higher yields of the desired products to be obtained, especially in the case of demanding polyfunctional molecules, including natural and biologically active compounds. Interactions between the FAH and the second‐generation ruthenium catalysts, which apparently improve the efficiency of the olefin metathesis transformation, have been studied by X‐ray structure analysis and computations, as well as by carrying out a number of metathesis experiments. The optimisation of reaction conditions by using an FAH can be regarded as a complementary approach for the design of new improved ruthenium catalysts. Fluorinated aromatic solvents are an attractive alternative medium for promoting challenging olefin metathesis reactions.

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Section: Resultsmentioning

confidence: 99%

The Doping Effect of Fluorinated Aromatic Solvents on the Rate of Ruthenium‐Catalysed Olefin Metathesis

Samojłowicz

Bieniek

Pazio

et al. 2011

Chemistry A European J

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“…49 Thus, selective tosylation of the primary alcohol was followed by in situ ring closure to an epoxide and ring-opening with lithium phenylacetylide to afford the alcohol 26 . 50 The overall yield was poor despite considerable optimization. t BuMe 2 Si (TBDMS) protection of 26 gave 27 , which underwent zirconocene-mediated cocyclization, dibromocarbenoid insertion, and phenylacetylide-driven zirconate rearrangement to give a 1:1 mixture of the exo and endo isomers 28 .…”

Section: Chemistrymentioning

confidence: 99%

“…A single-pot ring-closure/ring-opening procedure was used to convert pent-4-ene-1,2-diol into alcohol 26 . Thus, selective tosylation of the primary alcohol was followed by in situ ring closure to an epoxide and ring-opening with lithium phenylacetylide to afford the alcohol 26 . The overall yield was poor despite considerable optimization.…”

Section: Chemistrymentioning

confidence: 99%

Small Molecule Agonists of the Orphan Nuclear Receptors Steroidogenic Factor-1 (SF-1, NR5A1) and Liver Receptor Homologue-1 (LRH-1, NR5A2)

et al. 2011

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The crystal structure of LRH-1 ligand binding domain bound to our previously reported agonist 3-(E-oct-4-en-4-yl)-1-phenylamino-2-phenyl-cis-bicyclo[3.3.0]oct-2-ene 5 is described. Two new classes of agonists in which the bridgehead anilino group from our first series was replaced with an alkoxy or 1-ethenyl group were designed, synthesized, and tested for activity in a peptide recruitment assay. Both new classes gave very active compounds, particularly against SF-1. Structure-activity studies led to excellent dual-LRH-1/SF-1 agonists (e.g., RJW100) as well as compounds selective for LRH-1 (RJW101) and SF-1 (RJW102 and RJW103). The series based on 1-ethenyl substitution was acid stable, overcoming a significant drawback of our original bridgehead anilino-substituted series. Initial studies on the regulation of gene expression in human cell lines showed excellent, reproducible activity at endogenous target genes.

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