P‐Chirogenic Benzo‐Fused Phenoxaphosphane: Synthesis, Resolution and Study of the Stereochemical Properties of the Corresponding Palladium Complexes | Zendy

Doro Franco | Zendy; Lutz Martin | Zendy; Reek Joost N. H. | Zendy; Spek Anthony L. | Zendy; van Leeuwen Piet W. N. M. | Zendy

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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)

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