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Diastereoselective addition of organomanganese compounds to α-alkoxysubstituted propanals

  • Organometallic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Reactions of organomanganese compounds R1MnI (R1 = Ph, 4-MeC6H4-, Me, Bu,n-C7H15, BuC=C, PhOC), prepared from R1Li and Mnl2 in Et2O, with aldehydes MeCH(OR2)CHO (R2 = CH2Ph, CH2OMe, CH2OCH2Ph) affordthreo-alcohols MeCH(OR2)CH(OH)R1 with high diastereoselectivity. The interactions of phenylmanganese derivatives PhMnX (X = Cl, Br, I), Ph2Mn, and Ph3MnLi with 2-benzyloxypropanal were used as examples for studying the influence of reagent and solvent nature on addition diastereoselectivity.

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Authors and Affiliations

  1. Institute of Organic Chemistry, the Ural Branch, Russian Academy of Sciences, 450054, Ufa, Russian Federation

    A. N. Kasatkin, R. Kh. Biktimirov, I. P. Podlipchuk, V. R. Sultanmuratova & G. A. Tolstikov

Authors
  1. A. N. Kasatkin
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  2. R. Kh. Biktimirov
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  3. I. P. Podlipchuk
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  4. V. R. Sultanmuratova
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  5. G. A. Tolstikov
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Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 178–181, January, 1993.

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Kasatkin, A.N., Biktimirov, R.K., Podlipchuk, I.P. et al. Diastereoselective addition of organomanganese compounds to α-alkoxysubstituted propanals. Russ Chem Bull 42, 161–165 (1993). https://doi.org/10.1007/BF00700000

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  • DOI: https://doi.org/10.1007/BF00700000

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