CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2005, Vol. 77, No. 7, pp. 1259-1267

http://dx.doi.org/10.1351/pac200577071259

Asymmetric catalytic addition of diorganozinc reagents to imines: Scope and application

André B. Charette, Alessandro A. Boezio, Alexandre Côté, Elaine Moreau, Julien Pytkowicz, Jean-Nicolas Desrosiers and Claude Legault

Département de Chimie, Université de Montréal, Montréal H3C 3J7, Canada

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Kortmann Felix A., Chang Mu-Chieh, Otten Edwin, Couzijn Erik P. A., Lutz Martin, Minnaard Adriaan J.: Consecutive dynamic resolutions of phosphine oxides. Chem. Sci. 2014, 5, 1322. <http://dx.doi.org/10.1039/c3sc52913d>
  • Lu Di, Salem Geoff: Homochiral arsenic-/phosphorus-based ligands. Coordination Chemistry Reviews 2013, 257, 1026. <http://dx.doi.org/10.1016/j.ccr.2012.06.033>
  • Almansa Raquel, Collados Juan F., Guijarro David, Yus Miguel: Polymer-supported l-prolinol-based catalysts for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinyl)imines. Tetrahedron: Asymmetry 2013, 24, 116. <http://dx.doi.org/10.1016/j.tetasy.2012.12.007>
  • Zheng Haixing, Liu Qi, Wen Saishuai, Yang Hua, Luo Yiming: One-pot asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones catalyzed by amino acid-derived sulfonamides. Tetrahedron: Asymmetry 2013, 24, 875. <http://dx.doi.org/10.1016/j.tetasy.2013.05.028>
  • Nishimura Takahiro, Ashouri Akram, Ebe Yusuke, Maeda Yuko, Hayashi Tamio: Rhodium/chiral diene-catalyzed asymmetric methylation of N-sulfonylarylimines with trimethylboroxine. Tetrahedron: Asymmetry 2012, 23, 655. <http://dx.doi.org/10.1016/j.tetasy.2012.04.021>
  • Banerjee Sucharita, Smith Brad, Hitchcock Shawn R.: A dimethylzinc/diphenylphosphinoylimine approach to the asymmetric synthesis of the calcimimetic agent NPS R-568. Appl Organometal Chem 2011, 25, 105. <http://dx.doi.org/10.1002/aoc.1723>
  • Mei Haibo, Ji Xiaoyun, Han Jianlin, Pan Yi: Tetrabenzylhafnium as a New Organometallic Reagent for Imine Addition Resulting in α-Branched Amines. Eur J Org Chem 2011, 2011, 5783. <http://dx.doi.org/10.1002/ejoc.201100820>
  • Hussain Nusrah, Hussain Mahmud M., Ziauddin Muhammed, Triyawatanyu Plengchat, Walsh Patrick J.: Stereoselective Vinylation of Aryl N-(2-Pyridylsulfonyl) Aldimines with 1-Alkenyl-1,1-heterobimetallic Reagents. Org Lett 2011, 13, 6464. <http://dx.doi.org/10.1021/ol202766g>
  • Smith Elana A. Slutsky, Molev Gregory, Botoshansky Mark, Gandelman Mark: Modifiable bidentate systems via N–C rearrangement in triazoles. Chem Commun 2011, 47, 319. <http://dx.doi.org/10.1039/c0cc02033h>
  • Kumar Akshai, Samuelson Ashoka G.: Catalytic Reactions of Titanium Alkoxides with Grignard Reagents and Imines: A Mechanistic Study. Chem Asian J 2010, 5, 1830. <http://dx.doi.org/10.1002/asia.200900711>
  • Veverková Eva, Štrasserová Jana, Šebesta Radovan, Toma Štefan: Asymmetric Mannich reaction catalyzed by N-arylsulfonyl-l-proline amides. Tet Asymm 2010, 21, 58. <http://dx.doi.org/10.1016/j.tetasy.2009.12.013>
  • Crampton Rosemary H., Hajjaji Samir El, Fox Martin E., Woodward Simon: Reaction prospecting by 31P NMR: enantioselective rhodium-DuPhos catalysed addition of ZnMe2 to diphenylphosphinoylimines. Tet Asymm 2009, 20, 2497. <http://dx.doi.org/10.1016/j.tetasy.2009.09.020>
  • Trincado Mónica, Ellman Jonathan A.: Enantioselective Synthesis of α‐Aryl Alkylamines by Rh‐Catalyzed Addition Reactions of Arylboronic Acids to Aliphatic Imines. Angew Chem 2008, 120, 5705. <http://dx.doi.org/10.1002/ange.200801137>
  • Trincado Mónica, Ellman Jonathan A.: Enantioselective Synthesis of α‐Aryl Alkylamines by Rh‐Catalyzed Addition Reactions of Arylboronic Acids to Aliphatic Imines. Angew Chem Int Ed 2008, 47, 5623. <http://dx.doi.org/10.1002/anie.200801137>
  • Almansa Raquel, Guijarro David, Yus Miguel: Microwave-accelerated enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines catalysed by β-aminoalcohols with the prolinol skeleton. Tet Asymm 2008, 19, 1376. <http://dx.doi.org/10.1016/j.tetasy.2008.05.005>
  • Desrosiers Jean-Nicolas, Charette André B.: Catalytic Enantioselective Reduction of β,β-Disubstituted Vinyl Phenyl Sulfones by Using Bisphosphine Monoxide Ligands. Angew Chem 2007, 119, 6059. <http://dx.doi.org/10.1002/ange.200701367>
  • Desrosiers Jean-Nicolas, Charette André B.: Catalytic Enantioselective Reduction of β,β-Disubstituted Vinyl Phenyl Sulfones by Using Bisphosphine Monoxide Ligands. Angew Chem Int Ed 2007, 46, 5955. <http://dx.doi.org/10.1002/anie.200701367>
  • Cozzi Pier Giorgio, Hilgraf Robert, Zimmermann Nicole: Enantioselective Catalytic Formation of Quaternary Stereogenic Centers. Eur J Org Chem 2007, 2007, 5969. <http://dx.doi.org/10.1002/ejoc.200700318>
  • Almansa Raquel, Guijarro David, Yus Miguel: Nickel-catalysed addition of dialkylzinc reagents to N-phosphinoyl- and N-sulfonylimines. Tetrahedron 2007, 63, 1167. <http://dx.doi.org/10.1016/j.tet.2006.11.056>
  • El-Shehawy Ashraf A.: Synthesis of novel well-defined chain-end-functionalized polystyrenes with dendritic chiral ephedrine moieties and their applications as highly enantioselective diethylzinc addition to N-diphenylphosphinoyl arylimines. Tetrahedron 2007, 63, 11754. <http://dx.doi.org/10.1016/j.tet.2007.08.093>
  • Almansa Raquel, Guijarro David, Yus Miguel: N-Benzyl-l-prolinol: an efficient catalyst for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines. Tet Asymm 2007, 18, 896. <http://dx.doi.org/10.1016/j.tetasy.2007.03.026>
  • Yan Gexin, Wu Yong, Lin Wenqing, Zhang Xiaomei: Synthesis of novel chiral oxazoline ligands and application in the highly enantioselective diethylzinc addition to N-diphenylphosphinoylimines. Tet Asymm 2007, 18, 2643. <http://dx.doi.org/10.1016/j.tetasy.2007.10.035>
  • Almansa Raquel, Guijarro David, Yus Miguel: Enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines catalyzed by β-aminoalcohols with the prolinol skeleton. Tet Asymm 2007, 18, 2828. <http://dx.doi.org/10.1016/j.tetasy.2007.11.006>
  • Forrat Vicente J., Prieto Oscar, Ramón Diego J., Yus Miguel: trans-1-Sulfonylamino-2-isoborneolsulfonylaminocyclohexane Derivatives: Excellent Chiral Ligands for the Catalytic Enantioselective Addition of Organozinc Reagents to Ketones. Chem Eur J 2006, 12, 4431. <http://dx.doi.org/10.1002/chem.200501397>
  • Nishimura Takahiro, Yasuhara Yuichi, Hayashi Tamio: Asymmetric Addition of Dimethylzinc to N-Tosylarylimines Catalyzed by a Rhodium−Diene Complex toward the Synthesis of Chiral 1-Arylethylamines. Org Lett 2006, 8, 979. <http://dx.doi.org/10.1021/ol060213e>
  • Charette Andre B., Boezio Alessandro A., Cote Alexandre, Moreau Elaine, Pytkowicz Julien, Desrosiers Jean-Nicolas, Legault Claude: Asymmetric Catalytic Addition of Diorganozinc Reagents to Imines: Scope and Application. ChemInform 2005, 36. <http://dx.doi.org/10.1002/chin.200551257>