53877-58-0Relevant academic research and scientific papers
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.
SeO2-Mediated Oxidative Transposition of Pauson-Khand Products
Dibrell, Sara E.,Maser, Michael R.,Reisman, Sarah E.
supporting information, p. 6483 - 6487 (2020/04/30)
Oxidative transpositions of bicyclic cyclopentenones mediated by selenium dioxide (SeO2) are disclosed. Treatment of Pauson-Khand reaction (PKR) products with SeO2 in the presence or absence of water furnishes di- and trioxidized cyclopentenones, respectively. Mechanistic investigations reveal multiple competing oxidation pathways that depend on substrate identity and water concentration. Functionalization of the oxidized products via cross-coupling methods demonstrates their synthetic utility. These transformations allow rapid access to oxidatively transposed cyclopentenones from simple PKR products.
When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions
Laher, Romain,Marin, Christophe,Michelet, Véronique
supporting information, p. 4058 - 4062 (2020/04/20)
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.
Rhodium(i)-catalyzed Pauson-Khand-type reaction using formic acid as a CO surrogate: An alternative approach for indirect CO2 utilization
Lang, Xian-Dong,You, Fei,He, Xing,Yu, Yi-Chen,He, Liang-Nian
, p. 509 - 514 (2019/02/14)
Formic acid is found to be an ideal CO surrogate for the rhodium(i)-catalyzed Pauson-Khand-type (PK-type) reaction of various substituted 1,6-enynes to afford bicyclic cyclopentenones in moderate to good yields. High TON value of up to 263 and good results in the gram-scale experiment were also obtained, demonstrating the efficacy of this methodology. In addition, heterocyclic molecules of pharmaceutical importance were also furnished via inter- or intra-molecular hetero-PK-type reactions, further broadening the application of current strategy. In this protocol, formic acid was utilized as a bridging molecule for the conversion of CO2 to CO, since formic acid is manufactured via catalytic hydrogenation of CO2 and releases CO in the presence of acetic anhydride readily. Therefore, this methodology represents a green and indirect approach for chemical valorization of CO2 in the preparation of value-added compounds.
Atom-Economical Ni-Catalyzed Diborylative Cyclization of Enynes: Preparation of Unsymmetrical Diboronates
Cabrera-Lobera, Natalia,Quirós, M. Teresa,Brennessel, William W.,Neidig, Michael L.,Bu?uel, Elena,Cárdenas, Diego J.
, p. 6552 - 6556 (2019/08/20)
We report a Ni-catalyzed diborylative cyclization of enynes that affords carbo- and heterocycles containing both alkyl- and alkenylboronates. The reaction is fully atom-economical, shows a broad scope, and employs a powerful and inexpensive catalytic Ni-b
Ni-Catalyzed Cyclization of Enynes and Alkynylboronates: Atom-Economical Synthesis of Boryl-1,4-dienes
Cabrera-Lobera, Natalia,Quirós, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
, p. 14512 - 14516 (2019/11/11)
We report a novel atom-economical Ni-catalyzed cyclization reaction of enynes with alkynylboronates. The reaction employs a non-expensive Ni salt, a phosphine-based ligand and easy-handling alkynylboronates as boron–carbon source. The reaction provides co
Iron-Catalyzed Hydroborylative Cyclization of 1,6-Enynes
Cabrera-Lobera, Natalia,Rodríguez-Salamanca, Patricia,Nieto-Carmona, Juan C.,Bu?uel, Elena,Cárdenas, Diego J.
, p. 784 - 788 (2017/11/29)
We report first Fe-catalyzed hydroborylative cyclization reaction. The process provides one C?C and one C?B bond in a single operation and shows a wide scope, allowing the formation of carbo- and heterocycles containing a homoallylic boryl unit that can b
Electrochemical properties and reactions of organoboronic acid esters containing unsaturated bonds at their α-position
Ohtsuka, Kazuhiro,Inagi, Shinsuke,Fuchigami, Toshio
, p. G23 - G28 (2017/12/26)
Electrochemical analyses of 2-(cynnamyl)boronic acid pinacol ester and (3-phenyl-2-propynyl)boronic acid pinacol ester, and their trimethylsilyl analogues as well as their parent compounds were comparatively studied by cyclic voltammetry measurements. We
Cobalt-Catalyzed ortho-C?H Functionalization/Alkyne Annulation of Benzylamine Derivatives: Access to Dihydroisoquinolines
Martínez, ángel Manu,Rodríguez, Nuria,Gómez-Arrayás, Ramón,Carretero, Juan C.
supporting information, p. 11669 - 11676 (2017/08/30)
A practical picolinamide-directed C?H functionalization/alkyne annulation of benzylamine derivatives enabling access to the previously elusive 1,4-dihydroisoquinoline skeleton was developed using molecular O2 as the sole oxidant and Co(OAc)2 as precatalyst. The method is compatible with both internal and terminal alkynes and shows high versatility and functional-group tolerance. Furthermore, full preservation of enantiopurity is observed when using non-racemic α-substituted benzylamine derivatives. Kinetic analysis of the reagents and catalyst, labeling experiments, and the isolation and identification of catalytically competent Co-complexes revealed important insights about the mechanism.
Iron-catalyzed reductive cyclization of 1,6-enynes
Lin, Aijun,Zhang, Zhi-Wei,Yang, Jiong
, p. 386 - 389 (2014/04/03)
A precatalyst of FeCl2 and iminopyridine was activated in situ by a combination of diethylzinc and magnesium bromide etherate; it catalyzed the reductive cyclization of 1,6-enynes to give pyrrolidine and tetrahydrofuran derivatives from N-and O
