78776-44-0Relevant academic research and scientific papers
The construction of chiral fused azabicycles using a Pd-catalyzed allylic substitution cascade and asymmetric desymmetrization strategy
An, Qianjin,Liu, Delong,Shen, Jiefeng,Liu, Yangang,Zhang, Wanbin
supporting information, p. 238 - 241 (2017/11/27)
A highly enantioselective Pd-catalyzed asymmetric allylic substitution cascade of cyclic N-sulfonylimines with an accompanying asymmetric desymmetrization has been developed for the construction of fused tetrahydroindole derivatives bearing two chiral centers. Mechanistic studies confirmed that the cascade reaction proceeds by initial allylic alkylation and subsequent allylic amination. The first alkylation is a chirality-control step and represents an asymmetric desymmetrization of ciscyclic allyl diacetates. The reaction has been performed on a gram scale, and the desired products can take part in several transformations.
Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration
Shiramizu, Mika,Toste, F. Dean
supporting information, p. 12905 - 12909 (2014/01/06)
New modes of DODH: Oxorhenium compounds act as deoxydehydration(DODH)/acid dual-purpose catalysts to transform biomass-derived diol substrates into a variety of commodity chemical precursors. The power of this approach is highlighted by a tandem [1,3]-OH shift/DODH of 2-ene-1,4-diols and 2,4-diene-1,6-diols, and by a DODH/esterification sequence of sugar acids to unsaturated esters for the production of polymers and plasticizers. Copyright
Pd-catalyzed allylic alkylation cascade with dihydropyrans: Regioselective synthesis of furo[3,2- c ]pyrans
Bartlett, Mark J.,Turner, Claire A.,Harvey, Joanne E.
supporting information, p. 2430 - 2433 (2013/07/05)
A regioselective palladium-catalyzed allylic alkylation cascade forms furo[3,2-c]pyrans from various cyclic β-dicarbonyl bis-nucleophiles and 3,6-dihydro-2H-pyran bis-electrophiles. The combination of allylic carbonate and anomeric siloxy leaving groups in the dihydropyran substrate allows control of the many regiochemical possibilities in this reaction. Annulation proceeds stereoconvergently to give cis-fused furopyrans from either cis- or trans-substituted starting material.
Synthesis of 2-ene-1,4-diols by a new cascade-opening of 1,3-diepoxides: Towards an efficient synthesis of dihydroxytaxoid derivatives
Aldegunde, Maria J.,Castedo, Luis,Granja, Juan R.
supporting information; experimental part, p. 4785 - 4787 (2009/12/09)
The synthesis of dihydroxytaxoid derivatives, specially 2-Ene-1,4-diols using a new cascade-opening of 1,3-diepoxides was investigated. The study prepared a framework through a cascade ring-closing dienyne metathesis (RCDEYM) reaction from Dienyne. The me
Fast and mild palladium(II)-catalyzed 1,4-oxidation of 1,3-dienes via activation of molecular oxygen with a designed cobalt(II) porphyrin
Verboom, Renzo C.,Slagt, Vincent F.,Baeckvall, Jan-E.
, p. 1282 - 1284 (2008/09/16)
The use of a Co(porphyrin)-amide ligand, 2, in the palladium(II)-catalyzed 1,4-diacetoxylation of conjugated dienes under O2 results in aerobic oxidation. The catalyst was highly active under O2, and the 1,4-diacetoxylation reaction
Zeolite-encapsulated cobalt salophen complexes as efficient oxygen- activating catalysts in palladium-catalyzed aerobic 1,4-oxidation of 1,3- dienes
Woeltinger, Jens,Baeckvall, Jan-E.,Zsigmond, Agnes
, p. 1460 - 1467 (2007/10/03)
Different cobalt salophen catalysts 1, 2, 3, and 4 were prepared and studied as oxygen-activating agents in the palladium-quinone catalyzed aerobic oxidation of 1,3-dienes. These cobalt salophen catalysts were also encapsulated into the supercage of zeoli
Copper(II) mediated regioselective acetoxylation of allylic acetates and 1,4-diacetoxylation of alkenes
Macsari, Istvan,Szabo, Kalman J.
, p. 6345 - 6348 (2007/10/03)
Copper(II) chloride in presence of lithium chloride in acetic acid oxidizes allylic acetates with high regioselectivity. Tandem allylic C-H bond functionalization of unsubstituted alkenes could be accomplished by using copper(II) chloride/lithium chloride reagent together with catalytic amounts of palladium(II) salts.
REACTION OF 1,3-CYCLOHEXADIENE WITH THE ACETIC ACID-ACETIC ANHYDRIDE SYSTEM INITIATED BY MANGANESE(III) ACETATE
Melikyan, G. G.,Aslanyan, G. Kh.,Panosyan, G. A.,Kazaryan, P. I.,Badanyan, Sh. O.
, p. 222 - 226 (2007/10/02)
The reaction of 1,3-cyclohexadiene with the acetic acid-acetic anhydride system in the presence of manganese(III) acetate was studied.The reaction products were a mixture of the stereoisomers of 2-acetoxy-3-cyclohexenyl- and 4-acetoxy-2-cyclohexenylacetic acid and also 3,4- and 3,6-diacetoxy-1-cyclohexene.The mixture of acetoxy acids was converted into the corresponding hydroxy acids, and the diacetoxycyclohexenes were converted into the corresponding saturated esters.The cis-lactone was obtained as the only reaction product from the mixture of stereoisomersof the γ- and ε-hydroxy acids, while the methyl esters were obtained from the ε-hydroxy acids.
Allylic Carboxylations and Lactonization Using Benzoquinone and Hydrogen Peroxide or tert-Butyl Hydroperoxide as Oxidants
Akermark, Bjoern,Larsson, E. Magnus,Oslob, Johan D.
, p. 5729 - 5733 (2007/10/02)
Two new systems have been developed for catalytic carboxylation of alkenes.Both use palladium(II) as catalyst and benzoquinone as cocatalyst.In the first hydrogen peroxide was used as oxidant in acetic acid solution.Alkenes such as cyclohexene and 5-decene were converted cleanly to allylic acetates, but with 1-decene mainly the methyl ketone was formed.A diene such as 1,3-cyclohexadiene gave the diacetate while cis-1,2-divinylcyclohexane gave the cyclized monoacetate.In the second system, tert-butyl hydroperoxide was used as oxidant, permitting a wider choice of solvents and nucleophiles.Intramolecular reaction to lactones was possible in addition to allylic addition of acids such as benzoic, pivalic, and (S)-O-acetylmandelic acid.
