Electrochemical selenium- and iodonium-initiated cyclisation of hydroxy-functionalised 1,4-dienes
نویسندگان
چکیده
The cobalt(I)-catalysed 1,4-hydrovinylation reaction of allyloxytrimethylsilane and allyl alcohol with substituted 1,3-dienes leads to hydroxy-functionalised 1,4-dienes in excellent regio- and diastereoselective fashion. Those 1,4-dienols can be converted into tetrahydrofuran and pyran derivatives under indirect electrochemical conditions generating selenium or iodonium cations. The reactions proceed in good yields and regioselectivities for the formation of single diastereomers.
منابع مشابه
ADDITION OF UNSYMMETRICAL DIENES TO ACYL-1,4-BENZOQUINONES AND OXIDATION OF THE ADDUCTS WITH MANGANESE DIOXIDE: A REGIOSPECIFIC ROUTE TO MONO- AND DI-METHYL-1,4-NAPHTHOQUINONES
Regioselective Diels-Alder reactions of acyl-1,4-benzoquinones 1 with, severally, isoprene, trans-piperylene,1-acetoxy-1,3-butadiene and 1-methoxy-1,3-butadiene gave the corresponding adducts 2 in high yield. Treatment of the adducts 2 with manganese dioxide gave regiospecifically the corresponding 1,4-naphthoquinones 3. In several cases, the adducts of the acetylquinones afforded intermediates...
متن کاملRecent advances in the polymerization of butadiene over the last decade
The stereospecific polymerization of conjugated dienes began in 1954 with the first catalysts obtained by combining TiCl4 or TiCl3 with aluminum-alkyls, i.e. the catalytic systems previously employed for ethylene and propylene polymerizations. Subsequently, many other catalytic systems were obtained and examined by a combination of transition metal or lanthanide compounds with appropriate alkyl...
متن کاملA one-pot, reductive amination/6-endo-trig cyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids.
The first stereoselective synthesis of 2,6-trans-6-substituted-4-oxo-L-pipecolic acids using a tandem reductive amination/6-endo-trig cyclisation process is described. The sequential reduction and cyclisation mediated by sodium cyanoborohydride allowed the preparation of a series of highly functionalised 6-alkyl and 6-aryl analogues.
متن کاملThree-Component and Click Strategy for Synthesis of β-Hydroxy 1,4-Disubstituted 1,2,3-Triazoles Derivatives Catalyzed by 1,4-Dihydroxyanthraquinone-copper(II) Complex onto Nano AlPO4
In this work, copper(II) heterogeneous nanocatalyst supported on modified AlPO4 (Cu(II)-DA@Nano AlPO4) was used for the synthesis of some biological active heterocyclic molecules, particularly for the efficient conversion of a wide range of non-activated terminal alkynes to β-hydroxy 1,4-disubstituted 1,2,3-triazolethrough a three-component “click” reaction at room temperature in water. The reg...
متن کاملSynthesis of bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) derivatives functionalised with two, four or eight hydroxyl groups.
Short synthetic routes to a range of BEDT-TTF derivatives functionalised with two, four or eight hydroxyl groups are reported, of interest because of their potential for introducing hydrogen bonding between donor and anion into their radical cation salts. The cycloaddition of 1,3-dithiole-2,4,5-trithione with alkenes to construct 5,6-dihydro-1,3-dithiolo[4,5-b]1,4-dithiin-2-thiones is a key ste...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 11 شماره
صفحات -
تاریخ انتشار 2015