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Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 2111-2119

http://dx.doi.org/10.1351/pac200577122111

Enantioselective addition of organozinc reagents to carbonyl compounds

Miguel Yus and Diego J. Ramón

Instituto de Síntesis Orgánica y Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain

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  • Dobrikov Georgi M., Philipova Irena, Nikolova Rositsa, Shivachev Boris, Chimov Angel, Dimitrov Vladimir: Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes. Polyhedron 2012, 45, 126. <http://dx.doi.org/10.1016/j.poly.2012.06.090>
  • González-López Susana, Yus Miguel, Ramón Diego J.: Enantioselective synthesis of (+)-gossonorol and related systems using organozinc reagents. Tetrahedron: Asymmetry 2012. <http://dx.doi.org/10.1016/j.tetasy.2012.04.003>
  • Fernández-Mateos Emilio, Maciá Beatriz, Ramón Diego J., Yus Miguel: Catalytic Enantioselective Addition of MeMgBr and Other Grignard Reagents to Aldehydes. Eur J Org 2011, 2011, 6851. <http://dx.doi.org/10.1002/ejoc.201101283>
  • PraveenGanesh Nageswaran, de Candia Cristina, Memboeuf Antony, Lendvay György, Gimbert Yves, Chavant Pierre Y.: Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters. J Organomet Chem 2010, 695, 2447. <http://dx.doi.org/10.1016/j.jorganchem.2010.07.009>
  • Murtinho Dina, Elisa Silva Serra M., Rocha Gonsalves A.M.d’A.: Enantioselective ethylation of aldehydes with 1,3-N-donor ligands derived from (+)-camphoric acid. Tet Asymm 2010, 21, 62. <http://dx.doi.org/10.1016/j.tetasy.2009.12.012>
  • Forrat Vicente J., Ramón Diego J., Yus Miguel: Enantioselective addition of organozinc reagents to ketones catalyzed by grafted isoborneolsulfonamide polymers and titanium isopropoxide. Tet Asymm 2009, 20, 65. <http://dx.doi.org/10.1016/j.tetasy.2009.01.011>
  • Liu Ruochen, Bai Xuemei, Zhang Zhanbin, Zi Guofu: Efficient asymmetric addition of diethylzinc to aldehydes using 3-hydroxyazetidine derivatives as chiral ligands. Appl Organometal Chem 2008, 22, 671. <http://dx.doi.org/10.1002/aoc.1457>
  • El-Shehawy Ashraf A., Sugiyama Kenji, Hirao Akira: Application of well-defined chain-end-functionalized polystyrenes with dendritic chiral ephedrine moieties as reagents for highly catalytic enantioselective addition of dialkylzincs to aldehydes. Tet Asymm 2008, 19, 425. <http://dx.doi.org/10.1016/j.tetasy.2007.12.020>
  • Forrat Vicente J., Ramón Diego J., Yus Miguel: Toward the continuous-flow synthesis of chiral tertiary alcohols by enantioselective addition of organozinc reagents to ketones using nanosize isoborneol ligands. Tet Asymm 2008, 19, 537. <http://dx.doi.org/10.1016/j.tetasy.2008.02.002>
  • Martínez Ricardo, Zoli Luca, Cozzi Pier Giorgio, Ramón Diego J., Yus Miguel: Synthesis of camphorsulfonamide-based quinoline ligands and their N-oxides: first use in the enantioselective addition of organozinc reagents to aldehydes. Tet Asymm 2008, 19, 2600. <http://dx.doi.org/10.1016/j.tetasy.2008.10.020>
  • Zhang Zhanbin, Li Min, Zi Guofu: Synthesis of new chiralcis-3-hydroxyazetidines and their application in diethylzinc addition to aldehydes. Chirality 2007, 19, 802. <http://dx.doi.org/10.1002/chir.20470>
  • Bisai Alakesh, Singh Pradeep K., Singh Vinod K.: Enantioselective diethylzinc addition to aldehydes catalyzed by Ti(IV) complex of unsymmetrical chiral bis(sulfonamide) ligands of trans-cyclohexane 1,2-diamine. Tetrahedron 2007, 63, 598. <http://dx.doi.org/10.1016/j.tet.2006.11.022>
  • Forrat Vicente J., Ramón Diego J., Yus Miguel: First catalytic enantioselective synthesis of the cocaine abuse therapeutic agent (S)-(+)-1-(4-{2-[bis(4-fluorophenyl)methoxy]ethyl}piperazin-1-yl)-2-phenyl-2-propanol. Tet Asymm 2007, 18, 400. <http://dx.doi.org/10.1016/j.tetasy.2006.12.028>
  • Zhong Jiangchun, Guo Hongchao, Wang Mingan, Yin Mingming, Wang Min: Asymmetric diethylzinc addition and phenyl transfer to aldehydes using chiral cis-cyclopropane-based amino alcohols. Tet Asymm 2007, 18, 734. <http://dx.doi.org/10.1016/j.tetasy.2007.03.006>
  • Guillena Gabriela, Nájera Carmen, Ramón Diego J.: Enantioselective direct aldol reaction: the blossoming of modern organocatalysis. Tet Asymm 2007, 18, 2249. <http://dx.doi.org/10.1016/j.tetasy.2007.09.025>
  • 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>
  • Yus Miguel, Ramon Diego J.: Enantioselective Addition of Organozinc Reagents to Carbonyl Compounds. ChemInform 2006, 37. <http://dx.doi.org/10.1002/chin.200624239>
  • Guillena Gabriela, Ramón Diego J.: Enantioselective α-heterofunctionalisation of carbonyl compounds: organocatalysis is the simplest approach. Tet Asymm 2006, 17, 1465. <http://dx.doi.org/10.1016/j.tetasy.2006.05.020>
  • Forrat Vicente J., Ramón Diego J., Yus Miguel: Polymer supported trans-1-phenylsulfonylamino-2-isoborneolsulfonylaminocyclohexane ligand for the titanium catalyzed organozinc addition to ketones. Tet Asymm 2006, 17, 2054. <http://dx.doi.org/10.1016/j.tetasy.2006.07.038>