Hetero [4 + 2] Cycloadditions of (Trialkylsilyl)vinylketenes. Synthesis of α,β-Unsaturated δ-Valerolactones and -Lactams
✍ Scribed by Bennett, Dawn M.; Okamoto, Iwao; Danheiser, Rick L.
- Book ID
- 121878059
- Publisher
- American Chemical Society
- Year
- 1999
- Tongue
- English
- Weight
- 70 KB
- Volume
- 1
- Category
- Article
- ISSN
- 1523-7060
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📜 SIMILAR VOLUMES
An enantioselective synthesis of a,b-unsaturated gand d-lactams was proposed based on a simple strategy using the initial preparation of cis vinylogous aminoesters by the Horner reaction followed by a mild intramolecular cyclisation.
Treatment of a,P-unsaturated acid chlorides 5, 6, 14, 17, and 18 with NEt3 in toluene at reflux generates, stereo-and regiospecifically, the vinylketene which undergoes a facile intramolecular [2 + 21 cycloaddition.
γ-Oxo-α,β-unsaturated δ-lactones and lactams, which are in high yields, of the corresponding α-amino-γ-oxo-α,βunsaturated δ-lactones and -lactams, compounds of great easily accessible from their corresponding 2-furylcarbinols, were used as substrates for the 1,4-reductive addition of biological and