A Novel Concept for Combinatorial Chemistry in Solution: Synthesis of Highly Substituted Pyrrolidines by Multicomponent Domino Reactions

✍ Scribed by Lutz F. Tietze; Holger Evers; Enno Töpken

• Book ID: 102253487
• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: German
• Weight: 77 KB
• Volume: 85
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200290005

✦ Synopsis

Abstract

The multicomponent domino Knoevenagel hetero‐Diels____Alder hydrogenation process of N‐[(benzyloxy)carbonyl(Cbz)‐protected amino aldehydes with N,N‐dimethylbarbituric acid and the trimethylsilyl enol ethers 1–3 leads to the formation of the substituted pyrrolidines 12–15. Under the same conditions, reaction of the trimethylsilyl enol ether 4, obtained from acetophenone, gave the primary amines 18a,b probably due to a hydrogenolytic cleavage of the intermediately formed pyrrolidines. The zwitterionic products were obtained in high purity simply by precipitation with Et~2~O.