Synthesis and asymmetric polymerization of chiral maleimides bearing an aza crown ether
Chiral N-substituted maleimide derivatives bearing L-phenylalanine- or L-leucine-introduced aza crown ether ((S)-A15C5PAMI, (S)-A15C5LMI) were synthesized from maleic anhydride, corresponding amino acids and aza crown ether, and polymerized with an organometal/chiral ligand. The number-average-molec...
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| Published in | Polymer journal Vol. 43; no. 3; pp. 279 - 284 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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Nature Publishing Group
01.03.2011
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| Abstract | Chiral N-substituted maleimide derivatives bearing L-phenylalanine- or L-leucine-introduced aza crown ether ((S)-A15C5PAMI, (S)-A15C5LMI) were synthesized from maleic anhydride, corresponding amino acids and aza crown ether, and polymerized with an organometal/chiral ligand. The number-average-molecular weights and the specific optical rotations of the polymers were 700-5600 and -105.8° to -38.3°, respectively. The specific optical rotations of all polymers tended to a positive direction, compared with model compounds ((S)-A15C5PASI ([α]435 =-218.1°), (S)-A15C5LSI ([α]435 =-215.1°)). Asymmetric inductions in the main chains of the polymers were investigated by the measurements of specific optical rotation, circular dichroism. |
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| AbstractList | Chiral N-substituted maleimide derivatives bearing L-phenylalanine- or L-leucine-introduced aza crown ether ((S)-A15C5PAMI, (S)-A15C5LMI) were synthesized from maleic anhydride, corresponding amino acids and aza crown ether, and polymerized with an organometal/chiral ligand. The number-average-molecular weights and the specific optical rotations of the polymers were 700-5600 and -105.8° to -38.3°, respectively. The specific optical rotations of all polymers tended to a positive direction, compared with model compounds ((S)-A15C5PASI ([α]435 =-218.1°), (S)-A15C5LSI ([α]435 =-215.1°)). Asymmetric inductions in the main chains of the polymers were investigated by the measurements of specific optical rotation, circular dichroism. Chiral N-substituted maleimide derivatives bearing L-phenylalanine- or L-leucine-introduced aza crown ether ((S)-A15C5PAMI, (S)-A15C5LMI) were synthesized from maleic anhydride, corresponding amino acids and aza crown ether, and polymerized with an organometal/chiral ligand. The number-average-molecular weights and the specific optical rotations of the polymers were 700-5600 and -105.8 degree to -38.3 degree , respectively. The specific optical rotations of all polymers tended to a positive direction, compared with model compounds ((S)-A15C5PASI ([ alpha ] sub(435)=-218.1 degree ), (S)-A15C5LSI ([ alpha ] sub(435)=-215.1 degree )). Asymmetric inductions in the main chains of the polymers were investigated by the measurements of specific optical rotation, circular dichroism. |
| Author | OISHI, Tsutomu YAMABUKI, Kazuhiro IWAI, Jun ONIMURA, Kenjiro AZECHI, Motohisa |
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| Keywords | Substituent effect asymmetric polymerization Optically active polymer Nitrogen crown compound amino acid Oxazoline derivatives Chiral compound Sparteine Experimental study Asymmetric induction Lateral group Free radical polymerization Lithium Organic compounds maleimide Preparation Optical activity Maleimide derivative polymer Carboxamide Anionic polymerization Stereoelective polymerization Crown compound polymer aza crown ether |
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| Snippet | Chiral N-substituted maleimide derivatives bearing L-phenylalanine- or L-leucine-introduced aza crown ether ((S)-A15C5PAMI, (S)-A15C5LMI) were synthesized from... |
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| StartPage | 279 |
| SubjectTerms | Amino acids Applied sciences Asymmetry Bearing Crown ethers Derivatives Exact sciences and technology Optical properties Optical rotation Organic polymers Physicochemistry of polymers Polymerization Preparation, kinetics, thermodynamics, mechanism and catalysts |
| Title | Synthesis and asymmetric polymerization of chiral maleimides bearing an aza crown ether |
| URI | http://dx.doi.org/10.1038/pj.2010.139 https://www.proquest.com/docview/1030081486/abstract/ https://search.proquest.com/docview/1038238483 |
| Volume | 43 |
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