Asymmetric Synthesis of β2-Tryptophan Analogues via Friedel–Crafts Alkylation of Indoles with a Chiral Nitroacrylate

Asymmetric Synthesis of β2-Tryptophan Analogues via Friedel–Crafts Alkylation of Indoles with a Chiral Nitroacrylate

The asymmetric Friedel–Crafts alkylation of various indoles with a chiral nitroacrylate provides optically active β-tryptophan analogues after reduction of the nitro group and removal of the chiral auxiliary. This reaction generally occurs in good yield and high diastereoselectivity (up to 90:10)....

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2011-08, Vol.76 (15), p.6116-6124
Hauptverfasser: Pavlov, Nikola, Gilles, Pierre, Didierjean, Claude, Wenger, Emmanuel, Naydenova, Emilia, Martinez, Jean, Calmès, Monique
Format: Artikel
Sprache:eng
Schlagworte:
Acrylates - chemistry
Alkylation
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indoles - chemistry
Molecular Structure
Nitro Compounds - chemistry
Organic chemistry
Preparations and properties
Stereoisomerism
Tryptophan - chemical synthesis
Tryptophan - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The asymmetric Friedel–Crafts alkylation of various indoles with a chiral nitroacrylate provides optically active β-tryptophan analogues after reduction of the nitro group and removal of the chiral auxiliary. This reaction generally occurs in good yield and high diastereoselectivity (up to 90:10).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo200733t