Novel pathways for the formation of chiral binaphthyl polymers: Oxidative asymmetric phenolic coupling alone and in tandem with the Glaser-Hay coupling

Angewandte Chemie - International Edition

Volumn 42, Issue 19, 2003, Pages 2168-2170

  Xie, Xu ^a   Phuan, Puay Wah ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Asymmetric catalysis; Chirality; Copper; Coupling reactions; Polymerization

Indexed keywords

MOLECULAR ORIENTATION; OXIDATION; PHENOLS;

CHIRALITY;

ORGANIC POLYMERS;

NAPHTHYL GROUP; POLYMER;

ARTICLE; CATALYST; CHIRALITY; CIRCULAR DICHROISM; COUPLING FACTOR; ENANTIOSELECTIVITY; GEL PERMEATION CHROMATOGRAPHY; HALOGENATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; OPERON; OXIDATIVE PHOSPHORYLATION; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0037687372     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250325     Document Type: Article

References (21)

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14. One example of a polymerization by diastereoselective oxidative biaryl coupling of chiral BINOL derivatives has been reported: S. Habaue, T. Seko, Y. Okamoto, Macromolecules 2002, 35, 2437-2439.
15. We thank Andres Dulcey, Jonathon Ruddick, and Prof. Virgil Percec for assistance with the polymer characterization and Wai Leun Lau, Rachael S. Signarvic, and Prof. William DeGrado for assistance with the circular dichroism and UV measurements.
16. For similar structural effects with related polybinaphthyls see: a) S. R. Wyatt, Q.-S. Hu, X.-L. Yan, W. D. Bare, L. Pu, Macromolecules 2001, 34, 7983 - 7988; b) L. Ma, P. S. White, W. Lin, J. Org. Chem. 2002, 67, 7577-7586.
17. For similar structural effects with related polybinaphthyls see: a) S. R. Wyatt, Q.-S. Hu, X.-L. Yan, W. D. Bare, L. Pu, Macromolecules 2001, 34, 7983 - 7988; b) L. Ma, P. S. White, W. Lin, J. Org. Chem. 2002, 67, 7577-7586.
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