Lipase-catalyzed resolution of β-hydroxy selenides
作者： Michelangelo Gruttadauria , Paolo Lo Meo , Serena Riela , Francesca D’Anna , Renato Noto
DOI: 10.1016/J.TETASY.2006.10.010
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摘要: Abstract Eleven β-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene the presence of vinyl acetate at 30 °C. This approach provided, several cases, both enantiomers high enantiomeric excess. The role size substituents and behaviour cyclic is also discussed. Enantiopure are useful building blocks. As application this chemistry, enantiopure (1 S ,2 R )-indene oxide was obtained one step from proper selenide.
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sci-hub.se 参考文章(55)
Thomas Wirth, Organoselenium chemistry : modern developments in organic synthesis Springer. ,(2000)
Corwin Herman Hansch, Albert Leo, Substituent constants for correlation analysis in chemistry and biology Published in <b>1979</b> in New York NY) by Wiley. ,(1979)
D. A. Evans, J. Bartroli, T. L. Shih, Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates Journal of the American Chemical Society. ,vol. 103, pp. 2127- 2129 ,(1981) , 10.1021/JA00398A058
Chris H. Senanayake, F.Edward Roberts, Lisa M. DiMichele, Kenneth M. Ryan, Ji Liu, Laura E. Fredenburgh, Bruce S. Foster, Alan W. Douglas, Robert D. Larsen, Thomas R. Verhoeven, Paul J. Reider, The behavior of indene oxide in the ritter reaction: A simple route to cis-aminoindanol Tetrahedron Letters. ,vol. 36, pp. 3993- 3996 ,(1995) , 10.1016/0040-4039(95)00696-A
Michelangelo Gruttadauria, Carmela Aprile, Renato Noto, Stereocontrolled approach to δ- and γ-lactones and 1,3-diols. The role of X− ion in the selenolactonization Tetrahedron Letters. ,vol. 43, pp. 1669- 1672 ,(2002) , 10.1016/S0040-4039(02)00093-X
Michelangelo Gruttadauria, Paolo Lo Meo, Renato Noto, Regiochemical control in the synthesis of tetrahydrofurans by acid-catalyzed cyclization of hydroxy selenides and hydroxy sulfides Tetrahedron. ,vol. 55, pp. 4769- 4782 ,(1999) , 10.1016/S0040-4020(99)00149-0
Eric N. Jacobsen, Asymmetric catalysis of epoxide ring-opening reactions. Accounts of Chemical Research. ,vol. 33, pp. 421- 431 ,(2000) , 10.1021/AR960061V
Isamu Sugimoto, Satoshi Shuto, Akira Matsuda, A One-Pot Method for the Stereoselective Introduction of a Vinyl Group via an Atom-Transfer Radical-Cyclization Reaction with a Diphenylvinylsilyl Group as a Temporary Connecting Tether. Synthesis of 4‘α-C-Vinylthymidine, a Potent Antiviral Nucleoside1 Journal of Organic Chemistry. ,vol. 64, pp. 7153- 7157 ,(1999) , 10.1021/JO990787F
Benjamin S. Lane, Matthew Vogt, Victoria J. DeRose, Kevin Burgess, Manganese-catalyzed epoxidations of alkenes in bicarbonate solutions. Journal of the American Chemical Society. ,vol. 124, pp. 11946- 11954 ,(2002) , 10.1021/JA025956J
Montserrat Diéguez, Oscar Pàmies, Carmen Claver, Ligands derived from carbohydrates for asymmetric catalysis Chemical Reviews. ,vol. 104, pp. 3189- 3215 ,(2004) , 10.1021/CR0306889