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Pure Appl. Chem., 2006, Vol. 78, No. 5, pp. 977-983

http://dx.doi.org/10.1351/pac200678050977

Asymmetric cyanohydrin synthesis from aldehydes and ketones using chiral metal (salen) complex as catalyst

Sung Soo Kim

Department of Chemistry, Inha University, Incheon 402-751, South Korea

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  • Qiu Renhua, Chen Yi, Yin Shuang-Feng, Xu Xinhua, Au Chak-Tong: A mini-review on air-stable organometallic Lewis acids: synthesis, characterization, and catalytic application in organic synthesis. RSC Adv. 2012, 2, 10774. <http://dx.doi.org/10.1039/c2ra21517a>
  • Niemeyer Jochen, Kehr Gerald, Fröhlich Roland, Erker Gerhard: Salen Ligands Revisited: Synthesis and Application of a Planar Chiral “Ferro-Salen” Ligand. Eur J Inorg Chem 2010, 2010, 680. <http://dx.doi.org/10.1002/ejic.200901118>
  • Wang Wentao, Liu Xiaohua, Lin Lili, Feng Xiaoming: Recent Progress in the Chemically Catalyzed Enantioselective Synthesis of Cyanohydrins. Eur J Org Chem 2010, 2010, 4751. <http://dx.doi.org/10.1002/ejoc.201000462>
  • Niemeyer Jochen, Cloppenburg Jeannine, Fröhlich Roland, Kehr Gerald, Erker Gerhard: Salen-ligands based on a planar-chiral hydroxyferrocene moiety: Synthesis, coordination chemistry and use in asymmetric silylcyanation. J Organomet Chem 2010, 695, 1801. <http://dx.doi.org/10.1016/j.jorganchem.2010.04.008>
  • North Michael, Villuendas Pedro, Williamson Courtney: Mechanistic comparison of aluminium based catalysts for asymmetric cyanohydrin synthesis. Tetrahedron 2010, 66, 1915. <http://dx.doi.org/10.1016/j.tet.2010.01.004>
  • Belokon Yuri N., Clegg William, Harrington Ross W., Maleev Victor I., North Michael, Pujol Marta Omedes, Usanov Dmitry L., Young Carl: Mechanism-Guided Development of VO(salen)X Complexes as Catalysts for the Asymmetric Synthesis of Cyanohydrin Trimethylsilyl Ethers. Chem Eur J 2009, 15, 2148. <http://dx.doi.org/10.1002/chem.200801679>
  • Wang Jun, Wang Wentao, Li Wei, Hu Xiaolei, Shen Ke, Tan Cheng, Liu Xiaohua, Feng Xiaoming: Asymmetric Cyanation of Aldehydes, Ketones, Aldimines, and Ketimines Catalyzed by a Versatile Catalyst Generated from Cinchona Alkaloid, Achiral Substituted 2,2′-Biphenol and Tetraisopropyl Titanate. Chem. Eur. J. 2009, 15, 11642. <http://dx.doi.org/10.1002/chem.200900936>
  • Rajagopal Gurusamy, Kim Sung Soo: Synthesis of α-aryl nitriles through B(C6F5)3-catalyzed direct cyanation of α-aryl alcohols and thiols. Tetrahedron 2009, 65, 4351. <http://dx.doi.org/10.1016/j.tet.2009.03.073>
  • North Michael, Williamson Courtney: A bimetallic aluminium(salen) complex for asymmetric cyanohydrin synthesis. Tetrahetron Lett 2009, 50, 3249. <http://dx.doi.org/10.1016/j.tetlet.2009.02.028>
  • Madhavan Nandita, Weck Marcus: Highly Active Polymer-Supported (Salen)Al Catalysts for the Enantioselective Addition of Cyanide to α,β-Unsaturated Imides. Adv Synth Catal 2008, 350, 419. <http://dx.doi.org/10.1002/adsc.200700491>
  • Hatano Manabu, Ikeno Takumi, Matsumura Tokihiko, Torii Shinobu, Ishihara Kazuaki: Chiral Lithium Salts of Phosphoric Acids as Lewis Acid-Base Conjugate Catalysts for the Enantioselective Cyanosilylation of Ketones. Adv Synth Catal 2008, 350, 1776. <http://dx.doi.org/10.1002/adsc.200800314>
  • Seto Masaki, Roizen Jennifer L., Stoltz Brian M.: Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)-Tetrasubstituted Hydroxyketones, Acids, and Esters. Angew. Chem. 2008, 120, 6979. <http://dx.doi.org/10.1002/ange.200801424>
  • Seto Masaki, Roizen Jennifer L., Stoltz Brian M.: Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)-Tetrasubstituted Hydroxyketones, Acids, and Esters. Angew Chem Int Ed 2008, 47, 6873. <http://dx.doi.org/10.1002/anie.200801424>
  • Phosphomolybdic Acid Supported on Silica Gel as an Efficient and Reusable Catalyst for Cyanosilylation of Aldehydes. Bulletin of the Korean Chemical Society 2008, 29, 1320. <http://dx.doi.org/10.5012/bkcs.2008.29.7.1320>
  • Rajagopal Gurusamy, Kim Sung Soo, George Soney C.: Aluminum phthalocyanine: an active and simple catalyst for cyanosilylation of aldehydes. Appl Organometal Chem 2007, 21, 198. <http://dx.doi.org/10.1002/aoc.1189>
  • Kim Sung Soo, Rajagopal Gurusamy, George Soney C.: Solvent-free cyanosilylation of ketones with (CH3)3SiCN (TMSCN) catalyzed by NbF5. Appl Organometal Chem 2007, 21, 368. <http://dx.doi.org/10.1002/aoc.1204>
  • George Soney C., Kim Sung Soo, Rajagopal Gurusamy: Cyanosilylation of carbonyl compounds catalyzed by sodiumL-histidine. Appl Organometal Chem 2007, 21, 798. <http://dx.doi.org/10.1002/aoc.1278>
  • Jammi Suribabu, Rout Laxmidhar, Punniyamurthy Tharmalingam: Chiral linear polymers bonded alternatively with salen and 1,4-dialkoxy-2,6-diethynylbenzene: synthesis and application to diethylzinc addition to aldehydes. Tet Asymm 2007, 18, 2016. <http://dx.doi.org/10.1016/j.tetasy.2007.09.004>
  • Solvent-free Cyanosilylation of Carbonyl Compounds Catalyzed by NbCl5. Bulletin of the Korean Chemical Society 2007, 28, 1167. <http://dx.doi.org/10.5012/bkcs.2007.28.7.1167>
  • Asymmetric Cyanosilylation of Aldehydes by Chiral Ti-TADDOL Complex. Bulletin of the Korean Chemical Society 2006, 27, 1638. <http://dx.doi.org/10.5012/bkcs.2006.27.10.1638>
  • Aluminium Phthalocyanine: An Active and Simple Catalyst for Cyanosilylation of Ketones. Bulletin of the Korean Chemical Society 2006, 27, 1907. <http://dx.doi.org/10.5012/bkcs.2006.27.11.1907>