Synlett 2018; 29(16): 2171-2175
DOI: 10.1055/s-0037-1610551
cluster
© Georg Thieme Verlag Stuttgart · New York

Effect of Regioisomerism on the Efficiency of 1-Phenylpyrrole-Type Atropisomeric Amino Alcohol Ligands in Enantioselective Organometallic Reactions

Béla Mátravölgyi
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, P.O. Box 91, Hungary   Email: ffaigl@mail.bme.hu
,
Szilvia Deák
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, P.O. Box 91, Hungary   Email: ffaigl@mail.bme.hu
,
Zsuzsanna Erdélyi
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, P.O. Box 91, Hungary   Email: ffaigl@mail.bme.hu
,
Tamás Hergert
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, P.O. Box 91, Hungary   Email: ffaigl@mail.bme.hu
,
Péter Ábrányi-Balogh
b   Research Centre of Natural Sciences, Hungarian Academy of Sciences, 1519 Budapest, P.O. Box 286, Hungary
,
Ferenc Faigl*
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, P.O. Box 91, Hungary   Email: ffaigl@mail.bme.hu
› Author Affiliations
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.

Supporting Information

 
  • References and Notes

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