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Pure Appl. Chem., 1992, Vol. 64, No. 3, pp. 351-359

http://dx.doi.org/10.1351/pac199264030351

Metal, ligand and protective group tuning as a means to control selectivity

M. T. Reetz

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  • Wilcke David, Herdtweck Eberhardt, Bach Thorsten: SN 1-Type Substitution Reactions of N -Protected β-Hydroxytyrosine Esters: Stereoselective Synthesis of β-Aryl and β-Alkyltyrosines. Chem. Asian J. 2012, 7, 1372. <http://dx.doi.org/10.1002/asia.201101016>
  • Yoshinari Tomohiro, Gessier François, Noti Christian, Beck Albert K., Seebach Dieter: Stereoselective Preparation of 3-Amino-2-fluoro Carboxylic Acid Derivatives, and Their Incorporation in Tetrahydropyrimidin-4(1H)-ones, and in Open-Chain and Cyclic β-Peptides. J Helv Chim Acta 2011, 94, 1908. <http://dx.doi.org/10.1002/hlca.201100340>
  • REETZ M. T.: ChemInform Abstract: Metal, Ligand, and Protective Group Tuning as a Means to Control Selectivity. ChemInform 2010, 23, no. <http://dx.doi.org/10.1002/chin.199232280>
  • Bhuniya Debnath, Reddy D. Srinivasa, Hajare Atul K., Datrange Laxmikant S., Vyas Samir: Enantiospecific synthesis of sex pheromone of the obscure mealybug from pantolactone via tandem conjugate addition/cyclization. Tetrahetron Lett 2010, 51, 5291. <http://dx.doi.org/10.1016/j.tetlet.2010.07.166>
  • Hili Ryan, Baktharaman Sivaraj, Yudin Andrei K.: Synthesis of Chiral Amines Using α-Amino Aldehydes. Eur J Org Chem 2008, 2008, 5201. <http://dx.doi.org/10.1002/ejoc.200800604>
  • Reetz Manfred T., Griebenow Nils: Synthesis and Stereoselective CC Bond-forming Reactions of Peptide Aldehydes. Liebigs Ann /Recueil 2006, 1996, 335. <http://dx.doi.org/10.1002/jlac.199619960308>
  • Hoffmann Reinhard W.: Redox-Katalysatoren für Reduktionen mit unedlen Metallen. Angew Chem 2005, 117, 6433. <http://dx.doi.org/10.1002/ange.200501951>
  • Hoffmann Reinhard W.: Redox Catalysts for Reduction with Base Metals. Angew Chem Int Ed 2005, 44, 6277. <http://dx.doi.org/10.1002/anie.200501951>
  • Andrés JoséM., Pedrosa Rafael: Stereodivergent synthesis of all diastereomers of 4-aminoheptane-3,5-diol from (L)-serine. Tetrahedron 1998, 54, 5607. <http://dx.doi.org/10.1016/S0040-4020(98)00232-4>
  • Reetz Manfred T., Haning Helmut: Ligand effects in selective addition reactions of organoindium reagents with carbonyl compounds. J Organomet Chem 1997, 541, 117. <http://dx.doi.org/10.1016/S0022-328X(97)00021-1>
  • Merino Pedro, Lanaspa Ana, Merchan Francisco L., Tejero Tomas: Stereoselective grignard reactions to α-amino nitrones. Synthesis of optically active α-aminohydroxylamines and 1,2-diamines. Tet Asymm 1997, 8, 2381. <http://dx.doi.org/10.1016/S0957-4166(97)00250-4>
  • Reetz Manfred T, Strack Thomas J, Mutulis Felikss, Goddard Richard: Asymmetric dihydroxylation of chiral γ-amino α,β-unsaturated esters: Turning the mismatched into the matched case via protective group tuning. Tetrahetron Lett 1996, 37, 9293. <http://dx.doi.org/10.1016/S0040-4039(97)82945-0>
  • Hashimoto Yukihiko, Sato Yasushi, Takeshita Noriko, Kudo Kazuaki, Saigo Kazuhiko: Remote asymmetric induction using neighboring group participation of a sulfenyl group. Tetrahedron 1994, 50, 8317. <http://dx.doi.org/10.1016/S0040-4020(01)85555-1>
  • Szechner Barbara, Achmatowicz Osman, Gałdecki Zdzisław, Fruziński Andrzej: Synthesis and absolute configuration of four diastereoisomeric 1-(2-furyl)-2-aminobutane-1,3-diols. Tetrahedron 1994, 50, 7611. <http://dx.doi.org/10.1016/S0040-4020(01)90488-0>
  • Reetz Manfred T., Rölfing Karin, Griebenow Nils: A simple method for chelation controlled additions to α-amino aldehydes. Tetrahetron Lett 1994, 35, 1969. <http://dx.doi.org/10.1016/S0040-4039(00)73024-3>
  • Fringuelli F., Pellegrino R., Piermatti O., Pizzo F.: Chemoselective Oxidations in Water of Functional Groups. Synth Common 1994, 24, 2665. <http://dx.doi.org/10.1080/00397919408010580>
  • Frenking G., Köhler K.F., Reetz M.T.: On the origin of π-facial diastereoselectivity in nucleophilic additions to chiral carbonyl compounds 3. Rotational profiles of 2-methoxypropanal and 2-N,N-dimethylaminopropanal. Tetrahedron 1993, 49, 3971. <http://dx.doi.org/10.1016/S0040-4020(01)89911-7>
  • Branquet Eric, Durand Philippe, Vo-quang Liliane, Legoffic Fran¸ois: Methyl 3-N-Boc-amino-2,3,5-trideoxy-(α or β)-D-threo-pentofuranosidc and Methyl 2,3-dideoxy-3-N-Boc-amino-(α or β)-L-glycero-tetrofuranoside from L-serine and L-threonine. Nat Prod Lett 1993, 1, 239. <http://dx.doi.org/10.1080/10575639308050054>