Chiral polymer synthesis by means of repeated asymmetric reaction

Progress in Polymer Science (Oxford)

Volumn 30, Issue 5, 2005, Pages 540-558

  Itsuno, Shinichi ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

Aldol reaction; Allylation reaction; Asymmetric polymerization; Chiral polymers; Diels Alder reaction

Indexed keywords

CATALYST ACTIVITY; CHEMICAL BONDS; DECOMPOSITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SYNTHESIS (CHEMICAL);

ALDOL REACTION; ALLYLATION REACTION; ASYMMETRIC POLYMERIZATION; CHIRAL POLYMERS; DIELS-ALDER REACTION;

POLYMERS;

EID: 18444387697     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2005.01.008     Document Type: Review

References (84)

1. G.W. Coates Polymerization reaction E.N. Jacobsen A. Pfalts H. Yamamoto Comprehensive asymmetric catalysis vol. III 1999 Springer Berlin 1329 1349 [Chapter 36]
2. Y. Okamoto, and T. Nakano Asymmetric polymerization Chem Rev 94 1994 349 372
3. 3-symmetrical polymers Chem Eur J 5 1999 1898 1904
4. P. Pino Optically active addition polymers Adv Polym Sci 4 1965 393 456
5. G. Natta, M. Farina, and M. Donati Anionic catalytic systems for asymmetric synthesis of polymers Makromol Chem 43 1961 251 254
6. Y. Hayakawa, T. Fueno, and J. Furukawa Catalysts for asymmetric-induction polymerization of benzofuran. II. Properties and catalyses of some binary systems containing the menthoxy group J Polym Sci Part A-1 5 1967 2099 2109
7. G. Natta, M. Farina, M. Peraldo, and G. Bressan Asymmetric synthesis of optically active di-idotactic polymers from cyclic monomers Makromol Chem 43 1961 68 75
8. S. Bronco, G. Consiglio, R. Hutter, A. Batistini, and U.W. Suter Regio-, stereo-, and enantioselective alternating copolymerization of propene with carbon monoxide Macromolecules 27 1994 4436 4440
9. Z. Jiang, and A. Sen Palladium(II)-catalyzed isospecific alternating copolymerization of aliphatic.alpha.-olefins with carbon monoxide and isospecific alternating isomerization cooligomerization of a 1,2-disubstituted olefin with carbon monoxide synthesis of novel, optically active, isotactic 1,4- and 1,5-polyketones J Am Chem Soc 117 1995 4455 4467
10. K. Nozaki, N. Sato, and H. Takaya Highly enantioselective alternating copolymerization of propene with carbon monoxide catalyzed by a chiral phosphine-phosphite-palladium(ii) complex J. Am Chem Soc 117 1995 9911 9912
11. 2-symmetric bisoxazoline ligands J Am Chem Soc 116 1994 3641 3642
12. K. Nozaki, K. Nakano, and T. Hiyama Optically active polycarbonates: asymmetric alternating copolymerization of cyclohexene oxide and carbon dioxide J Am Chem Soc 121 1999 11008 11009
13. 2 with dimeric zinc complexes J Am Chem Soc 125 2003 5501 5510
14. 2 using homogeneous, zinc-based catalysts Chem Commun 2000 2007 2008
15. G.W. Coates Precise control of polyolefin stereochemistry using single-site metal catalysts Chem Rev 100 2000 1223 1252
16. R. Noyori Asymmetric catalysis via chiral metal complexes: selected examples; polymerization In: Asymmetric catalysis in organic synthesis 1994 Wiley New York [Chapter 4] p. 174-87
17. R. Noyori Asymmetric catalysis with purely organic compounds In: Asymmetric catalysis in organic synthesis 1994 Wiley New York [Chapter 7] p. 332-333
18. E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive asymmetric catalysis I-III 1999 Springer Berlin
19. J.K. Stille Diels-Alder polymerization Fortschr Hochpolym - Forsch 3 1961 48 58
20. G. Alhakimi, E. Klemm, and H. Görls Synthesis of new polyimides by Diels-Alder reaction of bis(2-pyrone)s with bismaleimides J Polym Sci, Part A, Polym Chem 33 1995 1133 1142
21. M. Wagner, W. Wohlfarth, and K. Müllen Anthracen- und anthrachinon-oligomere mit ortho-cyclophanverknupfung durch wiederholte Diels-Alder-reaction von 1,2,5,6-tetra-exo-methylencyclooctan Chimia 42 1988 377 380
22. U. Kumar, and T.X. Neeman Diels-Alder polymerization between bis(cyclopentadienones) and acetylenes. A versatile route to new highly aromatic polymers Macromolecules 28 1995 124 130
23. J.G. Smith, F. Sun, and R.M. Ottenbrite Preparation of polyimides utilizing the Diels-Alder reaction. 1,4-[N,N′-bis(butadienyl-2-methyl) diamido]-2,3,5,6-tetramethylbenzenes with bismaleimides Macromolecules 29 1996 1123 1130
24. C.I. Simionescu, and M. Grigoras Synthesis and polymerization of N-(1-anthryl) maleimide J Polym Sci, Part C, Polym Lett 28 1990 39 45
25. F.W. Harris, and J.K. Stille Diels-Alder polymers. Polyimides from a biscyclopentadienone and bismaleimides Macromolecules 1 1968 463 464
26. N. Kuramoto, K. Hayashi, and K. Nagai Thermoreversible reaction of diels-alder polymer composed of difurufuryladipate with bismaleimidodiphenylmethane J Polym Sci, Part A, Polym Chem 32 1994 2501 2504
27. Z.B. Shifrina, M.S. Averina, A.L. Rusanov, M. Wagner, and K. Mullen Branched polyphenylenes by repetitive Diels-Alder cycloaddition Macromolecules 33 2000 3525 3529
28. J.K. Stille, F.W. Harris, R.O. Rakutis, and H. Mukamal Diels-Alder polymerizations: polymers containing controlled aromatic segments J Polym Sci, Part B 4 1966 791 793
29. H. Mukamal, F.W. Harris, and J.K. Stille Diels-Alder polymers. III. Polymers containing phenylated phenylene units J Polym Soc, Part A-5 5 1967 2721 2729
30. J.K. Stille, and G.K. Noren Diels-alder polymers: Polyphenylenes containing alternating phenylene and triphenylphenylene units (1) J Polym Soc, Part B 7 1969 525 527
31. W. Wrasidlo, and J.M. Augl Preparation of poly(octaphenyl-tetraphenylene) J Polym Sci, Part B 7 1969 519 523
32. W. Ried, and D. Freitag Oligophenyls, oligophenylenes, and polyphenyls, a class of thermally very stable compounds Angew Chem Int Ed Engl 7 1968 835 844
33. J.K. Stille, R.O. Rakutis, H. Mukamal, and F.W. Harris Diels-Alder polymerizations. IV. Polymers containing short phenylene blocks connected by alkylene units Macromolecules 1 1968 431 436
34. G.K. Noren, and J.K. Stille Polyphenylenes Macromol Rev 5 1971 385 430
35. M. Kuhrau, and R. Stadler Synthesis of new polymers via Diels-Alder reaction, 2 soluble polymers via copolymerization Makromol Chem 193 1992 2861 2874
36. M. Kuhrau, and R. Stadler Synthesis of new polymers via Diels-Alder reaction Makromol Chem Rapid Commun 11 1990 635 644
37. A. Muller, and R. Stadler Mechanical and thermal behaviour of networks with 'flexible' and 'rigid' chains Macromol Chem Phys 197 1996 1373 1385
38. A. Muller, and R. Stadler Networks of partially hydrogenated cis-1,4-polybutadiene and 'rigid rods' Polym Int 41 1996 251 257
39. M. Kuhrau, and R. Stadler Synthesis of new polymers via Diels-Alder reaction. III. Biscyclohexadienephthalimide as dienes Polym Int 31 1993 71 80
40. C.D. Luiz Chiral Lewis acid catalysts in Diels-Alder cycloadditions: mechanistic aspects and synthetic applications of recent systems J Braz Chem Soc 18 1997 289 332
41. H. Kagan, and O. Riant Catalytic asymmetric Diels-Alder reactions Chem Rev 92 1992 1007 1019
42. U. Pindur, G. Lutz, and C. Otto Acceleration and selectivity enhancement of Diels-Alder reactions by special and catalytic methods Chem Rev 93 1993 741 761
43. L. Deloux, and M. Srebnik Asymmetric boron-catalyzed reactions Chem Rev 93 1993 763 784
44. M. Lautens, W. Klute, and W. Tam Transition metal-mediated cycloaddition reactions Chem Rev 96 1996 49 92
45. D.A. Evans, and J.S. Johnson Cycloaddition reactions E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive asymmetric catalysis III 1999 Springer Berlin 1177 1235 [Chapter 33]
46. J.E. Shaw, and D.C. Kunerth Quantitative conversion of carboxylic acids and phenols to esters and ethers by reaction of their salts with alkyl halides J Org Chem 39 1974 1968 1970
47. J. Bao, and W.D. Wulff Vaulted biaryls as chiral ligands for asymmetric catalytic Diels-Alder reactions J Am Chem Soc 115 1993 3814 3815
48. S. Itsuno, S. Tada, and K. Ito Asymmetric Diels-Alder polymerization using a chirally modified Lewis acid catalyst Chem Commun 1997 933 934
49. K. Kamahori, S. Tada, K. Ito, and S. Itsuno Optically active polymer synthesis by Diels-Alder polymerization with chirally modified Lewis acid catalyst Macromolecules 32 1999 541 547
50. J.J. Bahl, R.B. Bates, and B. Gordon III 2,3-Dimethylenebutadiene dianion; convenient procedure for allylic metalation of conjugated dienes J Org Chem 44 1979 2290 2291
51. A. Yanagisawa Allylation of carbonyl groups E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive asymmetric catalysis II 1999 Springer Berlin 965 982 [Chapter 27]
52. P.A.A. Klusener, L. Tip, and L. Brandsma On the direct metalation of isoprene Tetrahedron 47 1991 2041 2064
53. B. Guyot, J. Pornet, and L. Miginiac Le 2-trimethylsilylmethyl allyltrimethylsilane, precurseur de carbocycles et heterocycles a groupe methylenique Tetrahedron 47 1991 3981 3988
54. K. Olofsson, M. Larhed, and A. Hallberg Highly regioselective palladium-catalyzed internal arylation of allyltrimethylsilane with aryl triflates J Org Chem 63 1998 5076 5079
55. B.A. Narayanan, and W.H. Bunnelle The cerium mediated conversion of esters to allylsilanes Tetrahedron Lett 28 1987 6261 6264
56. K. Ishihara, M. Mouri, Q. Gao, T. Maruyama, K. Furuta, and H. Yamamoto Catalytic asymmetric allylation using a chiral (acyloxy)borane complex as a versatile Lewis acid catalyst J Am Chem Soc 115 1993 11490 11495
57. S. Aoki, K. Mikami, M. Terada, and T. Nakai Enantio- and diastereoselective catalysis of addition reaction of allylic silanes and stannanes to glyoxylates by binaphthol-derived titanium complex Tetrahedron 49 1993 1783 1792
58. 4 Angew Chem Int Ed Engl 35 1996 2363 2365
59. R.M. Angell, A.G.M. Barrett, D.C. Braddock, S. Swallow, and B.D. Vickery Enantioselective synthesis of homoallylic alcohols using (E)-but-2-enyl- trichlorosilane and chiral diamines Chem Commun 1997 919 920
60. M. Nakajima, M. Saito, M. Shiro, and S. Hashimoto (S)-3,3′- dimethyl-2,2′-biquinoline N,N′-dioxide as an efficient catalyst for enantioselective addition of allyltrichlorosilanes to aldehydes J Am Chem Soc 120 1998 6419 6420
61. A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y. Matsumoto, and H. Yamamoto Enantioselective addition of allylic trimethoxysilanes to aldehydes catalyzed by p-Tol-BINAP-AgF Angew Chem Int Ed Engl 38 1999 3701 3703
62. T. Kumagai, and S. Itsuno Asymmetric allylation polymerization: novel polyaddition of bis(allylsilane) and dialdehyde using chiral (acyloxy)borane catalyst Macromolecules 33 2000 4995 4996
63. T. Kumagai, and S. Itsuno Asymmetric polymerization of dialdehyde and bis(allylsilane) in the presence of chiral (acyloxy)borane catalyst Macromolecules 34 2001 7624 7628
64. S. Itsuno, and T. Kumagai Asymmetric synthesis of chiral polymers by means of repetitive addition of allylsilane to aldehyde Synthesis 2002 941 944
65. S. Itsuno, and T. Kumagai Asymmetric polymer synthesis by repetitive Sakurai-Hosomi allylation reaction of compounds possessing both formyl and allylsilane functions Helvetica Chim Acta 85 2002 3185 3196
66. T. Kumagai, and S. Itsuno Asymmetric allylation polymerization of bis(allylsilane) and dialdehyde containing Si-phenyl linkage Tetrahedron: Asymmetry 12 2001 2509 2516
67. T. Kumagai, and S. Itsuno Asymmetric allylation polymerization of bis(allylsilane) and dialdehyde containing arylsilane structure Macromolecules 35 2002 5323 5325
68. T. Mukaiyama Titanium tetrachloride in organic synthesis [New synthetic methods (21)] Angew Chem Int Ed Engl 16 1977 817 826
69. T. Mukaiyama, and S. Kobayashi Tin (II) enolates in the aldol, Michael, and related reactions Org React 46 1994 1 103
70. D.Y. Sogah, and O.W. Webster Sequential silyl aldol condensation in controlled synthesis of living poly(vinyl alcohol) precursors Macromolecules 19 1986 1775 1777
71. D.Y. Sogah, W.R. Hertler, I.B. Dicker, P.A. DePra, and J.R. Butera Catalyzed silicon-mediated living polymerizations. Structure control, catalyst design and mechanisms Makromol Chem Macromol Symp 32 1990 75 86
72. S. Itsuno, and H. Watanabe Asymmetric aldol polymerization of bis(triethylsilyl enol ether) and dialdehyde Polym Bull 51 2003 183 190
73. C.E. Peishoff, and W.L. Jorgensen Computer-assisted mechanistic evaluation of organic reactions. 4. Organosilicon chemistry J Org Chem 48 1983 1970 1979
74. K. Komura, N. Nishitani, and S. Itsuno A novel approach to the synthesis of optically active poly(β-hydroxy carbonyl)s by Aldol polymerization based on Mukaiyama Aldol reaction Polym J 31 1999 1045 1050
75. K. Komura, S. Itsuno, and K. Ito Aldol polymerization as a novel polyaddition based on Mukaiyama aldol reaction and its application to the synthesis of optically active polymer Chem Commun 1999 35 36
76. T. Mukaiyama The directed aldol reaction Org React 28 1982 203 343
77. S. Kiyooka, Y. Kaneko, M. Komura, H. Matsuo, and M. Nakano Enantioselective chiral borane-mediated aldol reactions of silyl ketene acetals with aldehydes. The novel effect of the trialkysilyl group of the silyl ketene acetal on the reaction course J Org Chem 56 1991 2268 2276
78. S. Kiyooka Development of chiral Lewis acid, oxazaborolidinone, promoted asymmetric aldol reaction J Synth Org Chem Jpn 55 1997 313 325
79. K. Ishihara, S. Kondo, and H. Yamamoto New and extremely active Corey's chiral oxazaborolidine catalyst Synlett 1999 1283 1285
80. K. Ishihara, S. Kondo, and H. Yamamoto Scope and limitations of chiral B-[3,5-bis(trifluoromethyl)phenyl]oxazaborolidine catalyst for use in the Mukaiyama Aldol reaction J Org Chem 65 2000 9125 9128
81. S. Itsuno, and K. Komura Highly stereoselective synthesis of chiral aldol polymers using repeated asymmetric Mukaiyama aldol reaction Tetrahedron 58 2002 8237 8246
82. Z. Jiang, and A. Sen Palladium(II)-catalyzed isospecific alternating copolymerization of aliphatic.alpha.-olefins with carbon monoxide and isospecific alternating isomerization cooligomerization of a 1,2-disubstituted olefin with carbon monoxide. Synthesis of novel, optically active, isotactic 1,4- and 1,5-polyketones J Am Chem Soc 117 1995 4455 4467
83. J.M. Seco, E. Quinora, and R. Riguera A practical guide for the assignment of the absolute configuration of alcohols, amines and carboxylic acids by NMR Tetrahedron: Asymmetry 12 2000 2915 2925
84. K. Komura, and S. Itsuno Asymmetric Aldol polymerization: synthesis of optically active polymers based on asymmetric Mukaiyama Aldol reaction Macromol Chem Phys 203 2002 931 936