Birch Reduction of Arenes as an Easy Entry to γ-Spirolactones
- A convenient method for the synthesis of γ-spirolactones in only 2–3 steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of ethylene oxide affords hydroxy acids, which undergo direct lactonization during work-up. Suitable precursors are methyl-substituted benzoic acids, naphthoic, and dicarboxylic acids. Subsequent hydrogenation proceeds smoothly with Pd/C as catalyst and saturated γ-spirolactones 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 with Raney nickel or Wilkinson's catalyst to obtain products with 1 double bond. Overall, more than 30 new γ-spirolactones have been synthesized in analytically pure form.
| Author details: | Tobias KrügerORCiDGND, Andrea BramborgGND, Alexandra Kelling, Eric SperlichORCiDGND, Torsten LinkerORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1002/ejoc.202101018 |
| ISSN: | 1434-193X |
| 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: | 2021/10/29 |
| Publication year: | 2021 |
| Release date: | 2022/07/18 |
| Tag: | Arenes; Birch reduction; Hydrogenation; Lactones; Synthetic methods |
| Volume: | 2021 |
| Issue: | 46 |
| Number of pages: | 9 |
| First page: | 6383 |
| Last Page: | 6391 |
| Funding institution: | University of Potsdam |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
