The chiro-Inositols and Related Cyclitols as Chiral Monomers for Polymerization: Expansion of a Family of Chiral Polymers

John F. Trant; Hollich Ho; Tomas Hudlicky

doi:10.1055/s-0034-1378563

Synlett, Table of Contents

Synlett 2014; 25(16): 2360-2364
DOI: 10.1055/s-0034-1378563

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The chiro-Inositols and Related Cyclitols as Chiral Monomers for Polymerization: Expansion of a Family of Chiral Polymers

John F. Trant

Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines ON, L2S 3A1, Canada Fax: +1(905)984-4841 Email: thudlicky@brocku.ca

,

Hollich Ho

Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines ON, L2S 3A1, Canada Fax: +1(905)984-4841 Email: thudlicky@brocku.ca

,

Tomas Hudlicky*

Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines ON, L2S 3A1, Canada Fax: +1(905)984-4841 Email: thudlicky@brocku.ca

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Abstract

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Abstract

Three different synthetic approaches to three different classes of oligomeric and polymeric inositol and inositol-like derivatives are presented: Grubbs cross-metathesis polymerization, Lewis acid catalyzed epoxide opening, and head-to-tail Diels–Alder polymerization. All three approaches lead to the formation of oligomers and polymers. The oligomers/polymers formed range from three (low-molecular-weight fraction of Diels–Alder polymerization) to 60 (Lewis acid catalyzed polymerization) repeats of inositol or inositol-like units. The molecular weights of the polymers were characterized by gel-permeation chromatography (GPC), MALDI, and NMR end-group analysis.

Key words

inositol polymers - Diels–Alder polymerization - epoxide polymerization - metathesis polymerization - carbocyclic polymers

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References

References
1 Zhang T, Franco P. Analytical and Preparative Potential of Immobilized Polysaccharide-Derived Chiral Stationary Phases. In Chiral Separation Techniques. Subramanian G. Wiley-VCH; Weinheim: 2007: 99
2 Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis. Shinichi I. John Wiley and Sons; Hoboken: 2011

3a Hudlicky T, Abboud KA, Entwistle DA, Fan R, Maurya R, Thorpe AJ, Bolonick J, Myers B. Synthesis 1996; 897
3b Hudlicky T, Abboud KA, Bolonick J, Maurya R, Stanton ML, Thorpe AJ. Chem. Commun. 1996; 1717
3c Paul BJ, Martinot TA, Willis J, Hudlicky T. Synthesis 2001; 952

4 Bui VP, Hudlicky T. Tetrahedron 2004; 60: 641
5 Hudlicky T, Luna H, Olivo HF, Andersen C, Nugent T, Price JD. J. Chem Soc., Perkin Trans. 1 1991; 2907

6a Mandel M, Hudlicky T. J. Chem. Soc., Perkin Trans. 1 1993; 741
6b Hudlicky T, Mandel M, Rouden J, Lee RS, Bachmann B, Dudding T, Yost KJ, Merola JS. J. Chem. Soc., Perkin Trans. 1 1994; 1553
6c Brammer LE. Jr, Hudlicky T. Tetrahedron: Asymmetry 1998; 9: 2011
6d Hudlicky T, Restrepo-Sànchez N, Kary PD, Jaramillo-Gomez LM. Carbohydr. Res. 2000; 324: 200

7a Nguyen BV, York C, Hudlicky T. Tetrahedron 1997; 53: 8807
7b Oppong KA, Hudlicky T, Yan F, York C, Nguyen BV. Tetrahedron 1999; 55: 2875

8 Hudlicky T, Pitzer KK, Stabile MR, Thorpe AJ, Whited GM. J. Org. Chem. 1996; 61: 4151

9a Hudlicky T, Reed JW. Chem. Soc. Rev. 2009; 38: 3117
9b Hudlicky T, Reed JW. Synlett 2009; 685
9c Duchek J, Adams DR, Hudlicky T. Chem. Rev. 2011; 111: 4223
9d Hudlicky T, Rulin F, Tsunoda T, Luna H, Andersen C, Price JD. Isr. J. Chem. 1991; 31: 229
9e Hudlicky T, Fan R, Luna H, Olivo H, Price J. Pure. Appl. Chem. 1992; 64: 1109
9f Hudlicky T. Efficient Synthesis of Optically Active Carbohydrates and other Oxygenated Compounds through Bio-Oxidation of Chlorinated Aromatics. In Enzymes in Organic Synthesis, NATO ASI Series C 381. Servi S. Kluwer Academic; Boston: 1992: 123
9g Hudlicky T, Reed JW. An Evolutionary Perspective of Microbial Oxidations of Aromatic Compounds in Enantioselective Synthesis: History, Current Status, and Perspectives. In Advances in Asymmetric Synthesis. Vol. 1. Hassner A. JAI Press; London: 1995: 271
9h Hudlicky T, Entwistle DA, Pitzer KK, Thorpe AJ. Chem. Rev. 1996; 96: 1220
9i Hudlicky T, Gonzalez D, Gibson DT. Aldrichimica Acta 1999; 32: 35
9j Hudlicky T. Biocatalytic Synthesis of Alkaloids and Carbohydrates: An Update. In Enzymes in Action. Zwanenburg B. Kluwer Academic; Dordrecht: 2000: 311

10 Werner L, Machara A, Hudlicky T. Adv. Synth. Catal. 2010; 352: 195
11 Varghese V, Hudlicky T. Angew. Chem. Int. Ed. 2014; 53: 4251
12 Endoma MA, Bui VP, Hansen J, Hudlicky T. Org. Process Res. Dev. 2002; 6: 525
13 Hudlicky T, Price JD, Rulin F, Tsunoda T. J. Am. Chem. Soc. 1990; 112: 9439
14 Carless HA. J. Tetrahedron Lett. 1992; 33: 6379
15 Deruyttere X, Dumortier L, Van der Eycken J, Vandewalle M. Synlett 1992; 51
16 Dumortier L, Liu P, Van der Eycken J, Vandewalle M In Carbohydrate Mimics: Concepts and Methods. Chapleur Y. Wiley-VCH; Weinheim: 1998: 209
17 Dumortier L, Van der Eycken J, Vandewalle M. Tetrahedron Lett. 1989; 30: 3201
18 Boyd DR, Sharma ND, Kaik M, Bell M, Berberian MV, McIntyre PB. A, Kelly B, Hardacre C, Stevenson PJ, Allen CC. R. Adv. Synth. Catal. 2011; 353: 2455

19a Sârbu T, Beckman EJ. Macromolecules 1999; 32: 6904
19b Bacskai R. J. Polym. Sci., Part A: Gen. Pap. 1963; 1: 2777
19c Gal Y.-S, Jung B, Lee W.-C, Choi S.-K. J. Macromol. Sci., Part A: Pure Appl. Chem. 1993; 30: 531

20a Vandenberg EJ. J. Polym Sci. 1960; 47: 486
20b Vandenberg EJ. J. Polym. Sci., Part A-1: Polym. Chem. 1969; 7: 525

21 Trant JF, Belding L, Dudding T, Hudlicky T. Helv. Chim. Acta 2012; 95: 2026

22a Satoh H, Mineshima A, Nakamura T, Teramoto N, Shibata M. React. Funct. Polym. 2014; 76: 49
22b Itsuno S, Tada S, Ito K. Chem. Commun. 1997; 933
22c Itsuno S. Prog. Polym. Sci. 2005; 30: 540
22d Bicu I, Mustaţă F. Angew. Makromol. Chem. 1999; 264: 21
22e Gandini A. Prog. Polym. Sci. 2013; 38: 1

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