Midland-Reduktion

Die Midland-Reduktion oder Midland-Alpine-Boran-Reduktion ist eine Namensreaktion in der organischen Chemie.[1][2] Die Reaktion ist nach dem Chemiker M.M. Midland benannt, welcher erstmals 1979 über die Reaktion berichtete.[3][4]

Übersichtsreaktion

Bei der Midland-Reduktion wird ein prochirales Keton oder ein Aldehyd durch das Alkylboran 1 enantioselektiv zu einem Alkohol reduziert.

Das Alkylboran 1 kann durch Reaktion von α-Pinen und 9-BBN mit THF synthetisiert werden:

Commons: Midland-Reduktion – Sammlung von Bildern, Videos und Audiodateien

Einzelnachweise

  1. László Kürti, Barbara Czakó: Strategic applications of named reactions in organic synthesis. Background and detailed mechanisms ; 250 named reactions. Elsevier Acad. Press, Amsterdam, Heidelberg 2009, ISBN 0-12-429785-4, S. 288–289 (englisch).
  2. Jie Jack Li: Name Reactions. A Collection of Detailed Reaction Mechanisms. Second Edition Auflage. Springer, Berlin, Heidelberg 2003, ISBN 978-3-662-05336-2, S. 262 (englisch).
  3. M. Mark Midland, Sue Greer, Alfonso Tramontano, Stephen A. Zderic: Chiral trialkylborane reducing agents. Preparation of 1-deuterio primary alcohols of high enantiomeric purity. In: J. Am. Chem. Soc. 101. Jahrgang, Nr. 9, 1979, S. 2352–2355, doi:10.1021/ja00503a019 (englisch).
  4. M. Mark Midland, Deborah C. McDowell, Robert L. Hatch, Alfonso Tramontano: Reduction of α,β-acetylenic ketones with B-3-pinanyl-9-borabicyclo[3.3.1]nonane. High asymmetric induction in aliphatic systems. In: J. Am. Chem. Soc. 102. Jahrgang, Nr. 2, 1980, S. 867–869, doi:10.1021/ja00522a083 (englisch).

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