Abstract:
New (1S,4S)-2,5-diazabicyclo[2.2.1]heptane derivatives synthesised by directed ortho metalation result in enantioselectivities of up to 78% e.e. when used as catalysts in the addition of diethylzinc to benzaldehyde.
Document Type:
Article
Language: English
Citation:
U. Jordis, M. Kesselgruber, S. Nerdinger, K. Mereiter, “New 2,5-diazabicyclo[2.2.1]heptanes and their application in the asymmetric addition of diethylzinc to benzaldehyde”, Mendeleev Commun., 9:4 (1999), 147–148
Linking options:
https://www.mathnet.ru/eng/mendc4568
https://www.mathnet.ru/eng/mendc/v9/i4/p147
This publication is cited in the following 7 articles:
Sergey N. Britvin, Andrey M. Rumyantsev, “Crystal structure of (1S,4S)-2,5-diazoniabicyclo[2.2.1]heptane dibromide”, Acta Crystallogr E Cryst Commun, 73:12 (2017), 1861
Andrea Gualandi, Stefano Grilli, Diego Savoia, “Octa‐1,7‐diene‐4,5‐diamine Derivatives: Useful Intermediates for the Stereoselective Synthesis of Nitrogen Heterocycles and Ligands for Asymmetric Catalysis”, Eur J Org Chem, 2016:19 (2016), 3143
Dieter Seebach, Uroš Grošelj, D. Michael Badine, W. Bernd Schweizer, Albert K. Beck, “Isolation and X‐Ray Structures of Reactive Intermediates of Organocatalysis with Diphenylprolinol Ethers and with Imidazolidinones”, Helvetica Chimica Acta, 91:11 (2008), 1999
Roberto Melgar‐Fernández, Rodrigo González‐Olvera, J. Luis Olivares‐Romero, Vianney González‐López, Leticia Romero‐Ponce, María del Refugio Ramírez‐Zárate, Patricia Demare, Ignacio Regla, Eusebio Juaristi, “Synthesis of Novel Derivatives of (1S,4S)‐2,5‐Diazabicyclo[2.2.1]heptane and Their Evaluation as Potential Ligands in Asymmetric Catalysis”, Eur J Org Chem, 2008:4 (2008), 655
Giuseppe Alvaro, Romano Di Fabio, Andrea Gualandi, Claudio Fiorelli, Magda Monari, Diego Savoia, Luca Zoli, “Stereoselective synthesis of substituted 2,5-diazabicyclo[2.2.1]heptanes by iodine-mediated cyclization of optically pure compounds containing the 4,5-diamino-1,7-octadiene and 1,2-diamino-4-alkene moieties”, Tetrahedron, 63:50 (2007), 12446
Claudio Fiorelli, Carla Marchioro, Gianluca Martelli, Magda Monari, Diego Savoia, “Iodine‐Mediated Cyclization of (4R,5R)‐4,5‐Diamino‐N,N′‐bis[(1S)‐1‐phenylethyl]‐1,7‐octadiene – A Stereoselective Route to 2,5‐Diazabicyclo[2.2.1]heptanes”, Eur J Org Chem, 2005:18 (2005), 3987
Ulrich Jordis, Martin Kesselgruber, Sven Nerdinger, Kurt Mereiter, “ChemInform Abstract: New 2,5‐Diazabicyclo[2.2.1]heptanes and Their Application in the Asymmetric Addition of Diethylzinc to Benzaldehyde.”, ChemInform, 30:45 (1999)
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