94532-07-7Relevant academic research and scientific papers
Acid-catalyzed reaction of 2-hydroxycyclobutanone with benzylic alcohols
Martis, Alberto,Luridiana, Alberto,Frongia, Angelo,Arca, Massimiliano,Sarais, Giorgia,Aitken, David J.,Guillot, Regis,Secci, Francesco
, p. 10053 - 10063 (2017/12/26)
The acid-promoted syntheses of 2-(benzyloxy)cyclobutanones and bis(benzyloxy)dioxatricyclo decanes were achieved starting from 2-hydroxycyclobutanone and variously functionalized benzyl alcohols. The reaction sequences afforded the desired products in good to high yields and in a solvent-dependent chemoselective fashion.
Asymmetric synthesis of O-protected acyloins using enoate reductases: Stereochemical control through protecting group modification
Winkler, Christoph K.,Stueckler, Clemens,Mueller, Nicole J.,Pressnitz, Desiree,Faber, Kurt
supporting information; experimental part, p. 6354 - 6358 (2011/02/24)
O-Protected cyclic acyloins were obtained in nonracemic form through asymmetric bioreduction of α,β-unsaturated alkoxy ketones by using 11 different enoate reductases from the "Old Yellow Enzyme" family. The stereochemical outcome of the biotransformation could be switched by variation of the O-protecting group or by the ring size of the substrate, which allows access to both stereoisomers in up to >97 % ee Whereas α-alkoxy enones were readily accepted as substrates, β-analogs were not converted. Overall, α-alkoxy enones represent a novel type of substrate for flavin-dependent ene-reductases. Copyright
Unprecedented in situ oxidative ring cleavage of isoxazolidines: Diastereoselective transformation of nitronic acids and derivatives into 3-hydroxymethyl 4-nitro tetrahydrofurans and pyrrolidines
Roger, Pierre-Yves,Durand, Anne-Catherine,Rodriguez, Jean,Dulcere, Jean-Pierre
, p. 2027 - 2029 (2007/10/03)
Equation presented. Nitronic acids undergo an intramolecular 1,3-dipolar cycloaddition to unactivated double bonds, and the resulting isoxazolidines spontaneously evolve by an unprecedented in situ oxidative ring cleavage. The extension of this transforma
CHEMISTRY OF α-NITROEPOXIDES: SYNTHESIS OF USEFUL INTERMEDIATES VIA NUCLEOPHILIC RING OPENING OF α-NITROEPOXIDES
Vankar, Yashwant D.,Shah, Kavita,Bawa, Anita,Singh, Surendra P.
, p. 8883 - 8906 (2007/10/02)
Various α-nitroepoxides are converted into corresponding 1,2-diketones via two different ways of ring opening viz. with Pd(O) and with DMSO/BF3*EtO2 (or ClSiMe3).In addition to this, a variety of nucleophiles are reacted with α-nitrocyclopentene oxide 6 and α-nitrocyclohexene oxide 7 to form the corresponding α-substituted ketones which are useful intermediates in organic synthesis.Two of the products so obtained viz. 32 and 33 are also transformed further into optically active thialactones 38 and 39 respectively via baker's yeast reduction followed by lactonisation.
Intramolecular Free Radical Cyclisations onto Enol Ethers. A General Synthesis of α-Alkyl-β-oxy- and α-Methylene-β-oxy-γ-butyrolactones
Begley, Michael J.,Landlow, Mark,Pattenden, Gerald
, p. 1095 - 1106 (2007/10/02)
Radical cyclisation of the enol ether bromoacetals (26), (28a-c), (29), and (37) in the presence of tributylstannane, produces precursors to the β-oxy-γ-butyrolactones (33), (34a-c), (35), and the α-methylene-β-oxy-γ-butyrolactone (39) in high overall yields.By contrast, treatment of (26) and (28a-b) with the cobalt(I) reagent derived from bis(dimethylglyoximato)(pyridine)cobalt(III) chloride (40), followed by oxidation of the intermediates (43) leads to the corresponding unsaturated β-oxy-γ-butyrolactones (42).
Synthesis of Cyclobutanated Butyrolactones via Copper(I)-Catalyzed Intermolecular Photocycloadditions of Homoallyl Vinyl or Diallyl Ethers
Ghosh, Subrata,Raychaudhuri, Swadesh R.,Salomon, Robert G.
, p. 83 - 90 (2007/10/02)
Intramolecular copper(I)-catalyzed 2? + 2? photocycloaddition provides an effective route for the synthesis of 2-oxa- and 3-oxabicycloheptanes from homoallyl vinyl or diallyl ethers, respectively.Ruthenium-catalyzed oxidation of these multicyclic tetrahydrofuran products provides a novel annulation of cyclobutanated butyrolactones.For intermediates incorporating both methine and methylene groups next to the tetrahydrofuran oxygen, a remarkable selectivity was found for oxidation at the methylene position.Highly stereoselective generation of exo-2-alkylsubstituted 3-oxabicycloheptanes occurred upon photobicyclization of diallyl ethers bearing an α-alkyl substituent.
INTRAMOLECULAR FREE RADICAL CYCLISATIONS ONTO VINYL ETHERS. A METHOD FOR THE SYNTHESIS OF β-OXY-γ-BUTYROLACTONES
Ladlow, Mark,Pattenden, Gerald
, p. 4317 - 4320 (2007/10/02)
Radical cyclisation of the vinyl ether bromides (2) and (7) in the presence of tri-n-butylstannane produces precursors to the β-oxy-γ-butyrolactones (6) and (9) in high yields (>80percent).By contrast, treatment of (2) and (7) with bis-(dimethylglyoximato)(pyridine)cobalt(I) chloride followed by oxidation of the intermediates (5) and (11) led to the corresponding unsaturated β-oxy-γ-butyrolactones (4) and (12) respectively.
