58130-12-4Relevant academic research and scientific papers
Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan
Hsu,Fang
, p. 8573 - 8584 (2007/10/03)
By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.
Regio- and stereoselectivity in the cyclization of enolates derived from 4,5-, 5,6-, and 6,7-epoxy-1-phenyl-1-alkanones. Competition between C- and O- alkylation
Crotti, Paolo,Di Bussolo, Valeria,Favero, Lucilla,Macchia, Franco,Pineschi, Mauro,Napolitano, Elio
, p. 5853 - 5866 (2007/10/03)
The results obtained in the base-catalyzed intramolecular cyclization of enolates derived from some representative 4,5-, 5-6, and 6,7-epoxy ketones and of the corresponding alkenes are discussed. The LHMDS/Sc(OTf)3 protocol on epoxy ketones app
Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones
Molander, Gary A.,Camera, Kimberly O.
, p. 830 - 846 (2007/10/02)
Lewis acids are employed as catalysts in the annulation of 1,4- and 1,5-dicarbonyl dielectrophiles with bis(trimethylsilyl) end ethers of β-diketones and β-keto esters. A variety of 2-(alkoxycarbonyl)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated. Unusually high regiocontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation reaction.
Synthese de methyl-8 dehydro-1,2 pyrrolizidines et de methyl-9 dehydro-1,2 indolizidines
Abbas, S. A.,Laurent, A.,Mison, P.,Pellissier, N.
, p. 288 - 296 (2007/10/02)
A synthetic route to the title compounds is described.It is based on the intramolecular cyclisation of hydroxy-Δ-3-pyrrolines 9, which are prepared in two steps from 2H-pyrroles 4.The stereoselectivity of the sequence can be controlled by changing the order of these two steps.
