Synthesis of gamma-spirolactams by Birch reduction of arenes

  • A convenient method for the synthesis of gamma-spirolactams in only three steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of chloroacetonitrile affords nitriles in moderate to good yields. Suitable precursors are methyl-substituted benzoic acids, naphthoic, and anthroic acid. Subsequent catalytic hydrogenation proceeds smoothly with PtO2 or Raney Ni as catalysts and lactams are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation at different pressures, affording products with 0, 1, or 2 double bonds. Overall, more than 15 new gamma-spirolactams have been synthesized in analytically pure form.

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Author details:Tobias KrügerORCiDGND, Torsten LinkerORCiDGND
Title of parent work (English):European journal of organic chemistry
Place of publishing:Weinheim
Publication type:Article
Date of first publication:2021/01/21
Publication year:2021
Release date:2023/01/25
Tag:Arenes; Birch reduction; Hydrogenation; Lactams; Synthetic methods
Number of pages:7
First page:1585
Last Page:1591
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
DDC classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer review:Referiert
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