[Zurück]

A Palvögyi, K. Schröder:
"Novel Carbamate-Based P,O-Ligands For Asymmetric Allylic Alkylations";
Poster: 21st European Symposium on Organic Chemistry, Wien; 14.07.2019 - 18.07.2019; in: "21st European Symposium on Organic Chemistry", PO-113 (2019), ISBN: 978-3-9504809-1-7; S. 121.

Highly funtionalized allylic compounds are invaluable intermediates for the pharmaceutical and agricultural industries. Since the early discovery of B. Trost and J. Tsuji, the field of Pd-catalysed asymmetric allylic alkylation (AAA) was growing rapidly. Due to its indisputible
advantages such as mild reaction conditions and operational simplicity it is still one of the most relevant strategy for the synthesis of substituted allylic compounds [1]. One current state-of-art ligand family (Trost-type ligands) relies on a chiral diamine core using a P,P-bidentate
motif for strong Pd-complexation, resulting in high catalytic activity and selectivity [1]. While such ligands are well estabilished and studied, monophosphine analogues with P,O-chelation did not gain much attention.
Herein, we report the synthesis of novel, chiral diamine-based P,O-ligands and their successful application in asymmetric allylic alkylations (AAA). After optimization of the reaction conditions, excellent yield and ee values have been obtained for aromatic and aliphatic substrates.
The results show that such a new chelation concept can compete or even outperform the current state-of-art catalyst systems.

https://publik.tuwien.ac.at/files/publik_286321.pdf