Enantioselective Induction of Helical Chirality in Cyclooctapyrroles by Metal-Complex Formation

Fixed chirality: The treatment of cyclooctapyrroles (see picture) with a metal source with optically active carboxylate or amine ligands leads to enantioselective metalation to give stereochemically stable helical mononuclear and dinuclear complexes without a chiral auxiliary. The helicity of the di...

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Published inAngewandte Chemie (International ed.) Vol. 48; no. 4; pp. 771 - 775
Main Authors Setsune, Jun-ichiro, Tsukajima, Aki, Okazaki, Naho, Lintuluoto, Juha M, Lintuluoto, Masami
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2009
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
Cobalt - chemistry
Copper - chemistry
Crystallography, X-Ray
helical structures
helicity
macrocycles
Molecular Conformation
Physical Sciences
porphyrinoids
Pyrroles - chemistry
Science & Technology
Stereoisomerism
transition metals
porphyrinoids
OCTAPHYRIN(1.1.1.1.1.1.1.1)
helicity
ABSOLUTE-CONFIGURATION
macrocycles
helical structures
transition metals
UNITS
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Summary:Fixed chirality: The treatment of cyclooctapyrroles (see picture) with a metal source with optically active carboxylate or amine ligands leads to enantioselective metalation to give stereochemically stable helical mononuclear and dinuclear complexes without a chiral auxiliary. The helicity of the dicopper complex was determined by the simulation of the CD spectrum on the basis of X‐ray crystallographic data.
Bibliography:http://dx.doi.org/10.1002/anie.200803538
This research was supported by a Grant‐in‐Aid for Scientific Research (No. 18550058) from the Ministry of Education, Culture, Sports, Science, and Technology (Japan). We are also grateful to the CREST program (Japan Science and Technology Agency) and the VBL project (Kobe University).
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200803538