A New Versatile Synthesis of Ring‐Substituted 2‐Cyclopropylglycines and Related Amino Acids

Alkyl 2‐chloro‐2‐cyclopropylideneacetates 2 serve as universal starting materials for a new general synthesis of cyclopro‐pylglycines by a simple three‐ to four‐step methodology. 1,4‐Addition of nucleophiles, substitution with azide ion, and mild catalytic deprotection lead to a variety of salt‐free...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemische Berichte 1992-04, Vol.125 (4), p.867-882
Hauptverfasser: Wessjohann, Ludger, Krass, Norbert, Yu, Dahai, Meijere, Armin De
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Alkyl 2‐chloro‐2‐cyclopropylideneacetates 2 serve as universal starting materials for a new general synthesis of cyclopro‐pylglycines by a simple three‐ to four‐step methodology. 1,4‐Addition of nucleophiles, substitution with azide ion, and mild catalytic deprotection lead to a variety of salt‐free cyclopropyl‐substituted amino acids in good yields, including the natural products 2‐(1‐methylcyclopropyl)glycine (4) and cleonin (5).
ISSN:0009-2940
1099-0682
DOI:10.1002/cber.19921250418