57187-82-3

Upstream product

• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 563-47-3 3-Chloro-2-methylpropene 
• 1458-98-6 2-methyl-3-bromo-1-propene 

Downstream Products

• 140605-82-9 5-methyl-1-phenylhex-5-en-1-yn-3-ol 

Relevant academic research and scientific papers

Oxygen-Tethered 1,6-Enynes and [41.0]-Bicyclic Ether Skeletons as Hedonic Materials for the Fragrance Industry

The synthesis of original structures for the fragrance industry bearing bicyclic scaffolds is described. To the best of our knowledge, these structures are not found in the fragrance industry, neither from natural nor synthetic pathways. NHC-gold-type catalysts showed excellent activities leading to light bicyclic enol ethers. Several bicyclic adducts were prepared in good to excellent yields (18-99%). Evaluation of NHC-Au complexes allowed to reach a TOF of 300 h -1. The evaluation for the organoleptic properties of [4.1.0]-bicyclic ethers were compared with the unprecedented properties of the 1,6-enyne precursors. Evaluations of starting materials showed a great interest in these structures with various olfactory facets. In this study, we depicted the similarity and differences between starting ethers and their cycloisomerized bicyclic counterparts.

Synthesis, Characterization, and Catalytic Activity of Chiral NHC Platinum(II) Pyridine Dihalide Complexes

A series of platinum(II) dihalide pyridine complexes bearing chiral C2-symmetric N-heterocyclic carbene (NHC) ligands [Pt(NHC*)(Py)(Hal)2] was synthesized in a one-pot procedure and characterized by NMR spectroscopy and single crystal X-ray diffraction (SC-XRD). The complexes were tested for the asymmetric cycloisomerization of enynol into bicyclo[3.1.0]hexanone and feature an excellent catalytic activity at room temperature along with a modest enantiomeric induction (up to 39% ee).

When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions

An efficient, and mild synthetic route for the preparation of functionalized volatile oxa-bicyclo[4.1.0]-hept-4-ene (29 compounds, 44-98% isolated yields) has been developed relying on the association of IPrAuCl with NaBArF. The remarkable selectivity was demonstrated on a 1 g and 25 g scale with low catalyst loadings. The synthetic utility of these low-molecular-weight enols was further demonstrated by the derivatization of some adducts and by the unprecedented olfactory evaluation of all bicyclic derivatives.

Palladium(0)-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides: A highly diastereoselective synthesis of tetrahydro-1H-cyclopenta [c] furans bearing two quaternary carbon centers

A new cascade process has been accomplished for the synthesis of tetrahydro-1H-cyclopenta[c]furans through palladium-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides. Notably, the key feature of this transformation is the use of vinyl bromides as the C1 building block. Various functionalized tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers could be obtained in good yields with excellent diastereoselectivities.

Palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: Facile synthesis of bicyclo[4.1.0]heptan-5-ones

We here describe a new palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes at room temperature using tBuONO as an oxidant for the synthesis of 3-bicyclo[4.1.0]heptan-5-ones. This cascade strategy involves the hydration, cyclization and cycl

Palladium-Catalyzed Radical Cascade Iododifluoromethylation/Cyclization of 1,6-Enynes with Ethyl Difluoroiodoacetate

A novel and convenient Pd-catalyzed radical cascade iododifluoromethylation/cyclization of 1,6-enynes with ethyl difluoroiodoacetate is demonstrated. The proposed transformation presents high stereoselectivity under mild and facile reaction conditions, th

Copper-Catalyzed Cascade Cyclization for the Synthesis of Trifluoromethyl-Substituted Spiro-2H-azirines from 1,6-Enynes

A method for the synthesis of trifluoromethyl CF3-substituted spirocyclic compounds containing with a unique quaternary carbon center from readily available starting materials has been developed. The reaction provides a facile access to 2H-azir

Lewis acid mediated intramolecular C-C bond formation of alkyne-epoxide leading to six-membered nitrogen and oxygen heterocycles

Intramolecular C-C bond formation of oxygen- and nitrogen-tethered alkynes and epoxide mediated by Lewis acid under ambient conditions is described. A simple procedure for the synthesis of 3,6- and 5,6-dihydropyrans and 3,4-dehydropiperidines from acyclic

Copper-catalyzed three-component cyanotrifluoromethylation/ azidotrifluoromethylation and carbocyclization of 1,6-enynes

A novel three-component strategy for the cyanotrifluoromethylation/ azidotrifluoromethylation and carbocyclization of 1,6-enynes is developed. The reaction proceeds smoothly under a moderate temperature by using a copper catalyst, which provides a rapid a

Copper-catalyzed trifluoromethylation-cyclization of enynes: Highly regioselective construction of trifluoromethylated carbocycles and heterocycles

Regioselective trifluoromethylation-cyclization: A method for copper-catalyzed trifluoromethylation-cyclization of simple enynes using the C-C triple bond as a nucleophile is reported for the first time (see scheme). The reaction proceeds efficiently in a