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Metal Complexes of Chiral Möbius Aromatic [28]Hexaphyrin(1.1.1.1.1.1): Enantiomeric Separation, Absolute Stereochemistry, and Asymmetric Synthesis
Author(s) -
Tanaka Takayuki,
Sugita Tsutomu,
Tokuji Sumito,
Saito Shohei,
Osuka Atsuhiro
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201002282
Subject(s) - metalation , chemistry , enantiomer , enantioselective synthesis , absolute configuration , stereochemistry , metal , molecule , combinatorial chemistry , organic chemistry , catalysis
Twist and sort out! Chiral separation of Pd II , Ni II , and Pt II complexes of [28]hexaphyrin(1.1.1.1.1.1) was achieved by HPLC on a chiral stationary phase (see inset for CD trace). The absolute configuration for the Pd II complex was determined by X‐ray crystallography. Asymmetric metalation of hexaphyrin, achieved with a Pd II binap salt, resulted in 23 % ee. This is the first example of asymmetric synthesis of Möbius‐twisted molecules.