C-Acylation under Virtually Neutral Conditions

✍ Scribed by Dr. Dee W. Brooks; Ms. Linda D.-L. Lu; Professor Dr. Satoru Masamune

• Book ID: 101549526
• Publisher: John Wiley and Sons
• Year: 1979
• Tongue: English
• Weight: 342 KB
• Volume: 18
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.197900722

✦ Synopsis

Recently, it was discovered['] that certain a-adamantyl car-bony1 compounds are considerably more active as antiviral agents and a great deal less toxic than 1 -aminoadamantane[2'. The multistep syntheses which were described in are based on phenols as starting materials, and are therefore restricted to the cyclohexanone framework. We wish to report that our method of a-tert-alkylation of carbonyl compounds can be applied generally to the introduction of 1 -adamantyl Silylenol ethers (2a)-( ), which are easily obtained from ketones (1 a)-(1 I I ) [ ~~, react smoothly with 1 -bromoadamantane in the presence of titanium tetrachloride at -40°C to -50°C to afford the desired a-adamantyl ketones (3) in good yields (Table ). Table shows that structurally