A New Non‐Cross‐Linked Polystyrene Supported 2‐Phenylimino‐2‐oxazolidine Chiral Auxiliary: Synthesis and Application in Asymmetric Alkylation Reactions
作者： Fu-Qiang Hu , De-Xin Xia , Cui-Fen Lu , Zu-Xing Chen , Gui-Chun Yang
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摘要: The synthesis of novel non-cross-linked polystyrene supported 2-phenylimino-2-oxazolidine is described, and its use as a chiral auxiliary in asymmetric alkylation reactions demonstrated by the several amides (>96 % ee). Furthermore, recovery recycling polymer-supported were successfully achieved without appreciable reduction yield or stereoselectivity.
sci-hub.se 参考文章(25)
Yadong Wan, Cuifen Lu, Junqi Nie, Guichun Yang, Zuxing Chen, Synthesis of Non-cross-linked Polystyrene Supported 5,5-dimethyl Oxazolidinone Chiral Auxiliary: Journal of Chemical Research-s. ,vol. 2007, pp. 84- 85 ,(2007) , 10.3184/030823407X198212
David A. Evans, Thomas C. Britton, Jon A. Ellman, Contrasteric carboximide hydrolysis with lithium hydroperoxide Tetrahedron Letters. ,vol. 28, pp. 6141- 6144 ,(1987) , 10.1016/S0040-4039(00)61830-0
Guido Giffels, Juliane Beliczey, Marcel Felder, Udo Kragl, Polymer enlarged oxazaborolidines in a membrane reactor: enhancing effectivity by retention of the homogeneous catalyst Tetrahedron-asymmetry. ,vol. 9, pp. 691- 696 ,(1998) , 10.1016/S0957-4166(98)00011-1
Giovanni Desimoni, Giuseppe Faita, Alessandro Galbiati, Dario Pasini, Paolo Quadrelli, Fabio Rancati, A soluble polymer-bound Evans’ chiral auxiliary: synthesis, characterization and use in cycloaddition reactions Tetrahedron: Asymmetry. ,vol. 13, pp. 333- 337 ,(2002) , 10.1016/S0957-4166(02)00117-9
David J. Ager, Indra Prakash, David R. Schaad, 1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis Chemical Reviews. ,vol. 96, pp. 835- 876 ,(1996) , 10.1021/CR9500038
Jian-Hong Yang, Gui-Chun Yang, Cui-Fen Lu, Zu-Xing Chen, Asymmetric synthesis of (2R,5S)-2-methyl-5-hexanolide, the sex pheromone of carpenter bee Xylocopa hirutissima Tetrahedron-asymmetry. ,vol. 19, pp. 2164- 2166 ,(2008) , 10.1016/J.TETASY.2008.08.026
Cuifen Lu, Donglai Li, Qiuyan Wang, Guichun Yang, Zuxing Chen, Stereoselective Synthesis of Sex Pheromone (R)‐4‐Methyl‐1‐Nonanol: Non‐Cross‐Linked Polystyrene Supported Oxazolidinone as a Chiral Auxiliary European Journal of Organic Chemistry. ,vol. 2009, pp. 1078- 1081 ,(2009) , 10.1002/EJOC.200800758
Tomoya Kotake, S Rajesh, Yoshio Hayashi, Yoshie Mukai, Mitsuhiro Ueda, Tooru Kimura, Yoshiaki Kiso, A new polymer-supported Evans-type chiral auxiliary derived from α-hydroxy-β-amino acid, phenylnorstatine: synthesis and application in solid-phase asymmetric alkylation reactions Tetrahedron Letters. ,vol. 45, pp. 3651- 3654 ,(2004) , 10.1016/J.TETLET.2004.03.043
Makoto Yamashita, Sang-Hyeup Lee, Guido Koch, Juerg Zimmermann, Bruce Clapham, Kim D. Janda, Solid-phase synthesis of oxazolones and other heterocycles via Wang resin-bound diazocarbonyls Tetrahedron Letters. ,vol. 46, pp. 5495- 5498 ,(2005) , 10.1016/J.TETLET.2005.06.061
David A. Evans, K. T. Chapman, J. Bisaha, Asymmetric Diels-Alder cycloaddition reactions with chiral .alpha.,.beta.-unsaturated N-acyloxazolidinones Journal of the American Chemical Society. ,vol. 110, pp. 1238- 1256 ,(1988) , 10.1021/JA00212A037