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Synthesis and Characterisation of a Novel Chiral Bidentate Pyridine‐N‐Heterocyclic Carbene‐Based Palladacycle
Author(s) -
Chiang Minyi,
Li Yongxin,
Krishnan Deepa,
Sumod Pullarkat,
Ng Kim Hong,
Leung PakHing
Publication year - 2010
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200901142
Subject(s) - chemistry , diastereomer , carbene , pyridine , denticity , stereochemistry , enantioselective synthesis , crystallization , medicinal chemistry , organic chemistry , crystal structure , catalysis
A novel chiral six‐membered bidentate pyridine‐N‐heterocyclic carbene palladacycle was prepared via optical resolution of the racemic palladacycle. This is the first successful demonstration of the synthesis of a chiral carbene palladacycle via fractional crystallization of its chiral amino acid derivatives. Upon formation of ( R C , S C ) and ( S C , S C )‐phenylalanate derivatives, the ( R C , S C )‐phenylalanate diastereomer crystallized out spontaneously. Optically active ( R )‐ and ( S )‐dichloropalladacycles can then be achieved by subsequent cleavage of the chiral amino acid auxiliary in the presence of aqueous HCl from their respective diastereomers. The absolute configurations of both the ( R )‐ and ( S )‐palladacycles were determined by X‐ray diffraction studies.