201861-56-5Relevant academic research and scientific papers
When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions
Laher, Romain,Marin, Christophe,Michelet, Véronique
, p. 4058 - 4062 (2020)
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.
Oxygen-Tethered 1,6-Enynes and [41.0]-Bicyclic Ether Skeletons as Hedonic Materials for the Fragrance Industry
Laher, Romain,Gentilini, Emilie,Marin, Christophe,Michelet, Véronique
, p. 4020 - 4029 (2021/08/10)
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.
Lewis acid mediated intramolecular C-C bond formation of alkyne-epoxide leading to six-membered nitrogen and oxygen heterocycles
Ghosh, Priya,Saha, Pipas,Bondalapati, Somasekhar,Indukuri, Kiran,Saikia, Anil K.
, p. 4119 - 4124 (2014/05/20)
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
Synthesis of oxacyclic dienes via ring-closing enyne metathesis: Difference in construction of eight-membered rings
Zhang, Lin-Lin,Zhang, Wen-Zhen,Ren, Xiang,Tan, Xin-Yan,Lu, Xiao-Bing
supporting information; experimental part, p. 3389 - 3392 (2012/07/28)
A series of oxacyclic diene compounds, especially eight-membered products bearing a single oxygen atom which have not been reported previously, were successfully synthesized via ring-closing enyne metathesis using the second-generation Grubbs catalyst. In contrast to the construction of the five-membered rings, completely opposite substrate selectivity that methyl substituted internal alkyne showed much higher reactivity than terminal alkyne was observed in building eight-membered ring derivatives.
