title: Synthesis of atropisomeric 1-phenylpyrrole-derived amino alcohols: new chiral ligands.
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.
authors.affiliation: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary. ffaigl@mail.bme.hu
authors.forename: Ferenc
authors.initials: F
authors.lastname: Faigl
authors.forename: Béla
authors.initials: B
authors.lastname: Mátravölgyi
authors.forename: Áron
authors.initials: Á
authors.lastname: Szöllősy
authors.forename: Mátyás
authors.initials: M
authors.lastname: Czugler
authors.forename: Gábor
authors.initials: G
authors.lastname: Tárkányi
authors.forename: Károly
authors.initials: K
authors.lastname: Vékey
authors.forename: Miklós
authors.initials: M
authors.lastname: Kubinyi
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D055620:Optical Phenomena; D011758:Pyrroles / Q000737:chemistry*; D012399:Rotation; D013237:Stereoisomerism; D013379:Substrate Specificity; D013816:Thermodynamics; D014961:X-Ray Diffraction
chemical_list: D000605:Amino Alcohols; D008024:Ligands; D011758:Pyrroles