Absolute Asymmetric Synthesis of Tertiary α-Amino Acids

Absolute Asymmetric Synthesis of Tertiary α-Amino Acids

Frozen: The spontaneous crystallization of an achiral compound in a chiral conformation is used as the unique source of chirality in an absolute asymmetric synthesis of tertiary amino acids. The dynamic axial chirality of tertiary aromatic amides is frozen in a crystal (see picture) and is responsib...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2012-05, Vol.51 (20), p.4981-4984
Hauptverfasser: Mai, Thi Thoa, Branca, Mathieu, Gori, Didier, Guillot, Régis, Kouklovsky, Cyrille, Alezra, Valérie
Format: Artikel
Sprache:eng
Schlagworte:
amides
amino acids
Amino Acids - chemical synthesis
Amino Acids - chemistry
asymmetric synthesis
Catalysis
chirality
Molecular Conformation
Molecular Structure
Stereoisomerism
synthetic methods
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Frozen: The spontaneous crystallization of an achiral compound in a chiral conformation is used as the unique source of chirality in an absolute asymmetric synthesis of tertiary amino acids. The dynamic axial chirality of tertiary aromatic amides is frozen in a crystal (see picture) and is responsible for the stereoselectivity of the deprotonation/alkylation (see scheme). α‐Amino acid derivatives are synthesized in up to 96 % ee.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201200950