132835-55-3Relevant academic research and scientific papers
STERICALLY GUIDED REARRANGEMENT OF 3,3-DISUBSTITUTED β-LACTONES. A RAPID CONSTRUCTION OF CYCLOHEPTANO TRANS-FUSED BUTYROLACTONES
Black, T. Howard,McDermott, Todd S.,Eisenbeis, Shane A.
, p. 6617 - 6620 (1990)
4-Cyclohexyl 3,3-disubstituted oxetan-2-ones rearrange under Lewis acid catalysis to afford trans-fused cycloheptano butyrolactones.
Pt-Catalyzed Rearrangement of Oxaspirohexanes to 3-Methylenetetrahydrofurans: Scope and Mechanism
Malapit, Christian A.,Chitale, Sampada M.,Thakur, Meena S.,Taboada, Rosa,Howell, Amy R.
, p. 5196 - 5209 (2015/05/27)
A novel Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans is reported. Mechanistic studies by 13C-labeling experiments confirm oxidative addition of Pt(II) regioselectively to the least substituted carbon-carbon bond
Low pressure carbonylation of heterocycles
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Page/Page column 4, (2008/06/13)
Heterocycles, e.g., epoxides, are carbonylated at low pressure with high percentage conversion to cyclic, ring expanded products using the catalyst where L is tetrahydrofuran (THF).
A new multicomponent reaction catalyzed by a [Lewis acid] +[Co(CO)4]- catalyst: Stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO
Church, Tamara L.,Byrne, Christopher M.,Lobkovsky, Emil B.,Coates, Geoffrey W.
, p. 8156 - 8162 (2008/02/08)
The use of mechanistic information to develop a new, catalytic multicomponent reaction is described. The complex [(salph)AI(THF) 2]+[Co(CO)4]- (1, salph = N,N′-o-phenylenebis(3,5-di-tert-butyl-salicylideneimine), THF = tetrahydrofuran), which is known to carbonylate epoxides, aziridines, and β-lactones, was used to catalyze the synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO. Under optimized conditions, the reaction was both selective and high-yielding. 1,3-Oxazinane-2,4-diones were synthesized from a variety of epoxides and isocyanates, including some epoxides that do not undergo simple ring-expansion carbonylation. The best results were obtained using highly electrophilic isocyanates. The mechanism of the multicomponent reaction was investigated using labeling and stereochemistry, and the data obtained were consistent with the 1-catalyzed formation of β-lactone and 1,3-oxazinane-2,4-dione from a common intermediate.
A novel synthesis of β-sulfinyl- and β-sulfonyl-hydroxamic acids via CsF-mediated ring opening of substituted β-lactones
Rossé,Gerber,Specklin,Hubschwerlen
, p. 538 - 540 (2007/10/03)
The ring-opening reaction of 3-substituted β-lactones with thiols was achieved using CsF in DMF as promoter. The resulting β-sulfanyl-carboxylic acid intermediates were coupled to hydroxylamine-Wang resin and the sulfur atom was selectively oxidized to afford β-sulfinyl- and β-sulfonyl-hydroxamic acid libraries.
Cationic palladium(II) complex-catalyzed [2 + 2] cycloaddition and tandem cycloaddition-allylic rearrangement of ketene with aldehydes: An improved synthesis of sorbic acid
Hattori, Tetsutaro,Suzuki, Yutaka,Uesugi, Osamu,Oi, Shuichi,Miyano, Sotaro
, p. 73 - 74 (2007/10/03)
Cationic palladium(II) complexes [PdL2(PhCN)2](BF4)2 efficiently catalyze the [2 + 2] cycloaddition of ketene with aldehydes to give the corresponding oxetan-2-ones, among which 4-vinyl-substituted ones are further isomerized under the conditions to give 3,6-dihydro-2H-pyran-2-ones in good yields.
A stereocomplementary approach to β-lactones: Highly diastereoselective synthesis of cis-β-lactones, a β-chloro acid, and a tetrahydrofuran
Wang, Yingcai,Zhao, Cunxiang,Romo, Daniel
, p. 1197 - 1199 (2008/02/09)
(matrix presented) In the course of mechanistic studies of the ZnCl2-mediated tandem Mukaiyama aldol-lactonization reaction of aldehydes and thiopyridyl ketene acetals, a stereocomplementary reaction employing SnCl4 was discovered. T
Catalyzed acyl halide-aldehyde cyclocondensations. New insights into the design of catalytic cross aldol reactions
Nelson, Scott G.,Wan, Zhonghui,Peelen, Timothy J.,Spencer, Keith L.
, p. 6535 - 6539 (2007/10/03)
Substoichiometric quantities (2.5-20 mol%) of Al(SbF6)3 catalyze the di(isopropyl)ethylamine-mediated cyclocondensation of various acyl halides and enolizable aldehydes to afford β-lactones in good yields (58-93%). These reactions ar
Process for producing a β-lactone derivative
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, (2008/06/13)
The present invention provides a process for producing a β-lactone derivative by reacting an aldehyde represented by formula (1): wherein R represents a C1-C15 alkyl group which may be substituted by an aryl group, a C2-C15 alkenyl group, a 5-7-membered a
