Synthesis of atropisomeric 1-phenylpyrrole-derived amino alcohols: new chiral ligands

Chirality
Ferenc FaiglMiklós Kubinyi

Abstract

An efficient synthetic method has been developed for the preparation of a new family of atropisomeric amino alcohols with 1-phenylpyrrole backbone. The synthesis is based on the different reactivities of the two carboxylic groups in optically active 1-[2-carboxy-6-(trifluoromethyl)phenyl]-1H-pyrrole-2-carboxylic acid (1). The chemical structures of the key intermediates were confirmed by spectroscopic methods and single crystal X-ray diffraction measurements. The very first application of a new optically active amino alcohol as catalyst for the enantioselective addition of diethylzinc to benzaldehyde demonstrated the practical usefulness of atropisomeric compounds in which there are six-atom chains between the two functional groups.

References

Aug 14, 2003·Chemical Reviews·Pavel KocovskýMartin Smrcina
May 27, 2011·Organic & Biomolecular Chemistry·Carlos ArrónizMercedes Amat

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