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Synlett 2018; 29(16): 2171-2175
DOI: 10.1055/s-0037-1610551
DOI: 10.1055/s-0037-1610551
cluster
Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions
This work was supported through funding from the National Research, Development and Innovation Office of Hungary (NKFIH) PD129652, K104528 and the Richter Gedeon Talentum Foundation.Further Information
Publication History
Received: 03 May 2018
Accepted after revision: 08 July 2018
Publication Date:
25 July 2018 (online)
Published as part of the Cluster Atropisomerism
Abstract
Syntheses of two regioisomeric series of atropisomeric amino alcohols and a comparative study on their application in the enantioselective addition of diethylzinc to benzaldehyde are reported. Systematic modification of the electronic and steric properties of the functional groups resulted in highly efficient catalyst ligands in both series. Quantum-chemical calculations agreed well with the experimental results of this first systematic comparative study on regioisomeric atropisomeric ligands.
Key words
atropisomerism - amino alcohols - enantioselectivity - asymmetric catalysis - phenylpyrrole - ligandsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610551.
- Supporting Information
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References and Notes
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