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.
Author details: | Tobias KrügerORCiDGND, Torsten LinkerORCiDGND |
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DOI: | https://doi.org/10.1002/ejoc.202100056 |
ISSN: | 1099-0690 |
Title of parent work (English): | European journal of organic chemistry |
Publisher: | Wiley-VCH |
Place of publishing: | Weinheim |
Publication type: | Article |
Language: | English |
Date of first publication: | 2021/01/21 |
Publication year: | 2021 |
Release date: | 2023/01/25 |
Tag: | Arenes; Birch reduction; Hydrogenation; Lactams; Synthetic methods |
Volume: | 2021 |
Issue: | 10 |
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 |