A practical method for the large-scale synthesis of diastereomerically pure (2R,5S)-3-phenyl-2-(8-quinolinoxy)-1,3-diaza-2-phosphabicyclo-[3.3.0]- octane Ligand (QUIPHOS). Synthesis and X-ray structure of its corresponding chiral π-allyl palladium complex

Journal of Organic Chemistry

Volumn 64, Issue 24, 1999, Pages 8940-8942

  Brunel, Jean Michel ^a   Constantieux, Thierry ^a   Buono, Gérard ^a  

^a Ecole Centrale Marseille   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 PHENYL 2 (8 QUINOLINOXY) 1,3 DIAZA 2 PHOSPHABICYCLO[3.3.0]OCTANE; CYCLOALKANE DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; MOLECULAR MODEL; NOTE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033607709     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990205u     Document Type: Note

References (32)

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29. The synthesis of the (2S,5R) enantiomer of ligand 7 may be envisionned according to the same experimental procedure using commercially available D-glutamic acid. For application of L- and D-glutamic acid in asymmetric synthesis, see: Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis; Wiley-Interscience: New York, 1987; p 216.
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31. -3. All of the measurements were made on a Rigaku diffractometer with Mo Kα radiation. Cell constants and the orientation matrix for data collection were obtained from a least-squares refinement using setting angles of 30 reflections in the range θ = 1-25° for Z = 4. A total of 2695 reflections were collected at T = 298 K and R = 0.052 for the refined structure. The standards were measured after every 120 reflections. Among the first 200 pairs of reflections, the signs of the corresponding calculated differences established that the molecule is described with the correct absolute configuration R at the phosphorus atom. Moreover, it has been verified that crystallization does not occur to provide individual crystals of different stereoisomers of complex 8.
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