6.17 C–O Bond Formation: Acylation of meso Diols

作者: T. Furuta , T. Kawabata

DOI: 10.1016/B978-0-08-095167-6.00619-4

关键词: CarbeneStereochemistryImidazolePlanar chiralityAcylationAmidineOrganic chemistryMoleculeChemistryDesymmetrizationAxial chirality

摘要: Acylative desymmetrization of meso diols has attracted significant attention since it is useful for preparing optically active functionalized molecules in a single manipulation. Herein, recent aspects organocatalytic asymmetric acylation are described. Chiral organocatalysts, including chiral phosphines, 4-dimethylaminopyradine (DMAP) derivatives, imidazole N -heterocyclic carbene tertiary amines, and amidine derivatives acylative diols, Typical examples enzymatic also included.

参考文章(79)
Jin-Li Cao, Jin Qu, Desymmetrization of meso-1,2-diols via the dynamic kinetic resolution of its monodichloroacetates. Journal of Organic Chemistry. ,vol. 75, pp. 3663- 3670 ,(2010) , 10.1021/JO100435F
E. Peter Kündig, Thierry Lomberget, Ryan Bragg, Cyril Poulard, Gérald Bernardinelli, Desymmetrization of a meso-diol complex derived from [Cr(CO)3(η6-5,8-naphthoquinone)]: use of new diamine acylation catalysts Chemical Communications. ,vol. 39, pp. 1548- 1549 ,(2004) , 10.1039/B404006F
Robert Chênevert, Ghodsi Mohammadi Ziarani, Marie Pascale Morin, Mohammed Dasser, Enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines. Chemoenzymatic synthesis of (5S,9S)-(+)-indolizidine 209D Tetrahedron-asymmetry. ,vol. 10, pp. 3117- 3122 ,(1999) , 10.1016/S0957-4166(99)00315-8
Isamu Shiina, Kenya Nakata, Keisuke Ono, Yu-suke Onda, Makoto Itagaki, Kinetic Resolution of Racemic α-Arylalkanoic Acids with Achiral Alcohols via the Asymmetric Esterification Using Carboxylic Anhydrides and Acyl-Transfer Catalysts Journal of the American Chemical Society. ,vol. 132, pp. 11629- 11641 ,(2010) , 10.1021/JA103490H
Shinya Mizuta, Takeo Tsuzuki, Tetsuya Fujimoto, Iwao Yamamoto, Catalytic asymmetric desymmetrization of cyclic meso-1,3- and 1,4-diols by a phosphinite derivative of quinidine. Organic Letters. ,vol. 7, pp. 3633- 3635 ,(2005) , 10.1021/OL051129M
Vladimir B. Birman, Eric W. Uffman, Hui Jiang, Ximin Li, Corey J. Kilbane, 2,3-Dihydroimidazo[1,2-a]pyridines: A New Class of Enantioselective Acyl Transfer Catalysts and Their Use in Kinetic Resolution of Alcohols Journal of the American Chemical Society. ,vol. 126, pp. 12226- 12227 ,(2004) , 10.1021/JA0491477
E. Vedejs, N. S. Bennett, L. M. Conn, S. T. Diver, M. Gingras, S. Lin, P. A. Oliver, M. J. Peterson, Tributylphosphine-catalyzed acylations of alcohols: scope and related reactions Journal of Organic Chemistry. ,vol. 58, pp. 7286- 7288 ,(1993) , 10.1021/JO00077A064
J. L. Gustafson, D. Lim, S. J. Miller, Dynamic Kinetic Resolution of Biaryl Atropisomers via Peptide-Catalyzed Asymmetric Bromination Science. ,vol. 328, pp. 1251- 1255 ,(2010) , 10.1126/SCIENCE.1188403
Scott J. Miller, Gregory T. Copeland, Nikolaos Papaioannou, Thomas E. Horstmann, Elizabeth M. Ruel, Kinetic Resolution of Alcohols Catalyzed by Tripeptides Containing the N-Alkylimidazole Substructure Journal of the American Chemical Society. ,vol. 120, pp. 1629- 1630 ,(1998) , 10.1021/JA973892K
Vladimir B. Birman, Ximin Li, Benzotetramisole:  A Remarkably Enantioselective Acyl Transfer Catalyst Organic Letters. ,vol. 8, pp. 1351- 1354 ,(2006) , 10.1021/OL060065S