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P‐Chirogenic Benzo‐Fused Phenoxaphosphane: Synthesis, Resolution and Study of the Stereochemical Properties of the Corresponding Palladium Complexes
Author(s) -
Doro Franco,
Lutz Martin,
Reek Joost N. H.,
Spek Anthony L.,
van Leeuwen Piet W. N. M.
Publication year - 2008
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.200700887
Subject(s) - chemistry , enantiopure drug , stereocenter , diastereomer , palladium , absolute configuration , chiral resolution , resolution (logic) , stereochemistry , ring (chemistry) , phosphorus , enantioselective synthesis , organic chemistry , enantiomer , catalysis , artificial intelligence , computer science
The synthesis and resolution of chiral phenoxaphosphane 3 , with the stereogenic center at the phosphorus atom, is described. Compound 3 has been synthesized following a well‐known procedure for trapping a phosphorus atom within a six‐membered ring. The resolution of the racemic mixture of 3 was achieved through separation of its diastereomeric palladacycle derivatives 7a , b and 9a , b . The absolute configuration of enantiopure phosphanes 3a , b was assigned unequivocally by means of X‐ray crystal structure determination for complex 9a and by combination of NOE( 1 H– 1 H)/COSY( 1 H, 1 H) spectroscopy and DFT calculations for complexes 7a , b , which in both cases led to identical results. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)