Simple Synthesis of gamma-Spirolactams by Birch Reduction of Benzoic Acids
- A convenient synthesis of gamma-spirolactams in only two steps was developed. Birch reduction of benzoic acids and immediate alkylation with chloroacetonitrile afforded cyclohexadienes in high yields. The products could be isolated by crystallization on a large scale in analytically pure form. Subsequent hydrogenation with platinum(IV) oxide as the catalyst reduced the nitrile functionality and the double bonds in the same step with excellent stereoselectivity. The relative configurations were determined unequivocally by X-ray analyses. Direct cyclization of the intermediary formed amino acids afforded the desired gamma-spirolactams in excellent overall yields. The procedure is characterized by few steps, cheap reagents, and can be performed on a large scale, interesting for industrial processes.
| Author details: | Tobias KrügerORCiDGND, Alexandra Kelling, Uwe SchildeORCiDGND, Torsten LinkerORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1002/ejoc.201601650 |
| 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: | 2016/12/30 |
| Publication year: | 2016 |
| Release date: | 2022/06/24 |
| Tag: | Diastereoselectivity; Hydrogenation; Lactams; Reduction; Synthetic methods |
| Issue: | 6 |
| Number of pages: | 4 |
| First page: | 1074 |
| Last Page: | 1077 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
