36884-29-4Relevant articles and documents
Synthesis and olfactory characterization of silicon-containing derivatives of the acyclic lily-of-the-valley odorant 5,7,7-trimethyl-4-methylideneoctanal
D?rrich, Steffen,Mahler, Christoph,Tacke, Reinhold,Kraft, Philip
, p. 1675 - 1687 (2015/02/18)
5-Methyl-4-methylidene-6-(trimethylsilyl)hexanal (1b), a sila analog of the acyclic lily-of-the-valley odorant 5,7,7-trimethyl-4-methylideneoctanal (1a), and the Si-containing derivatives 2-6 were prepared in multistep syntheses, starting from Cl3SiH and Cl2SiMe2 , respectively. Compounds 1b, 2-6, and their new precursors were characterized by elemental analyses (C, H, N) and NMR spectroscopic studies (1H, 13C, 15N, and 29Si). To gain more information about the structure-odor correlation in the family of lily-of-the-valley or muguet odorants, C/Si analogs 1a/1b and derivatives 2-6 were evaluated for their olfactory properties.
Nucleophilic substitution reaction at an sp2 carbon of vinyl halides with an intramolecular thiol moiety: synthesis of thio-heterocycles
Lei, Mao-Yi,Xiao, Yong-Jun,Liu, Wei-Min,Fukamizu, Koji,Chiba, Shunsuke,Ando, Kaori,Narasaka, Koichi
experimental part, p. 6888 - 6902 (2009/12/06)
This article presents a full account of intramolecular vinylic substitution reactions of bromoalkenes having an acetylthio moiety, which give sulfur-containing heterocycles such as dihydrothiophene, tetrahydrothiopyran, and 2-alkylidenethietane derivative
Synthesis of the 3-methylene-2-vinyltetrahydropyran unit; the hallmark of the sesquiterpene, hodgsonox
Barlow, Anna J.,Compton, Benjamin J.,Weavers, Rex T.
, p. 2470 - 2475 (2007/10/03)
(Chemical Equation Presented) The synthesis of some simple compounds containing the previously unreported 3-methylene-2-vinyltetrahydropyran system, a unique feature of the liverwort metabolite, hodgsonoxis reported. Key features are the creation of an ac
Efficient stereochemical relay en route to leucascandrolide A.
Kozmin
, p. 755 - 758 (2007/10/03)
[structure: see text]. A complete relay of the initial stereochemical information is central to the efficient and highly stereocontrolled construction of the C1-C15 fragment of the marine macrolide leucascandrolide A. Cyclic silane 3, assembled via Pt-cat
Asymmetric catalysis. Asymmetric catalytic intramolecular hydroacylation of 4-pentenals using chiral rhodium diphosphine catalysts
Barnhart, Richard W.,Wang, Xianqi,Noheda, Pedro,Bergens, Steven H.,Whelan, John,Bosnich
, p. 1821 - 1830 (2007/10/02)
Catalysts of the type [Rh(chiral diphosphine)]+ convert 4-substituted 4-pentenals into the corresponding 3-substituted cyclopentanones with generally high turnover numbers and frequencies at 25 °C. The enantioselectivities of various substituted 4-pentenals with two chiral diphosphines have been explored. It was found that with the binap catalyst, almost complete enantioselectivity is observed for 4-pentenal substrates bearing 4-substituted tertiary substituents and for ester groups. Ketonic substituents give very high enantioselectivities. The mechanism of intramolecular hydroacylation has been explored, and it is suggested that an important consideration for obtaining high turnover frequencies is related to the acyl-alkyl reductive elimination mechanism which is inferred to occur by a process similar to ester hydrolysis. The origin of the enantioselection is discussed in terms of the interactions between the phenyl groups of the phosphine and the substituent of the pentenal.
Synthesis of Bicyclic Nitrogen Compounds via Tandem Intramolecular Heck Cyclization and Subsequent Trapping of Intermediate ?-Allylpalladium Complexes
Harris, G. Davis,Herr, R. Jason,Weinreb, Steven M.
, p. 5452 - 5464 (2007/10/02)
Intramolecular palladium-mediated three-component cyclization of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed.The methodology has been applied to construction of both fused and bridged bicyclic systems.The strategy can also be used for spirocyclizations.This chemistry involves regiospecific generation of ?-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.
