✦ LIBER ✦
Preparation of Resin-Bound N-(α-Methoxyalkyl)amides: An Advantageous Use of Solid-Phase Chemistry for the Handling of Unstable Precursors of the Versatile N-Acyliminium Ions
✍ Scribed by Cécile Vanier; Alain Wagner; Charles Mioskowski
- Publisher
- John Wiley and Sons
- Year
- 2001
- Tongue
- English
- Weight
- 149 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
The development of a new and efficient synthesis of resin-bound N-(alpha-methoxyalkyl)amides is described. The condensation of aldehydes on a supported amide in the presence of trimethyl orthoformate afforded, in acidic media, the resin-bound N-acyliminium ion precursors. Repeating the reaction a second time led to a great improvement in yields, demonstrating one advantage of the solid-phase chemistry for the handling of sensitive intermediates difficult to isolate.