Polymer-supported chiral diol as ligand of Ti(IV) for enantioselective Diels-Alder reaction

Chirality

Volumn 9, Issue 2, 1997, Pages 191-197

  Irurre, José ^a   Fernández Serrat, Anna ^a   Rosanas, Francesc ^a  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

Author keywords

chiral Lewis acid; Diels Alder; enantioselective; polymer supported; polystyrene divinylbenzene; TADDOL; titanium complexes

Indexed keywords

BENZENE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; DIMETHYL SULFOXIDE; POLYMER; PYRIDINE DERIVATIVE; TETRAHYDROFURAN;

ALKYLATION; CATALYST; CHIRALITY; COMPLEX FORMATION; CONFERENCE PAPER; DRUG EFFICACY; DRUG SYNTHESIS; ENANTIOMER; LIGAND BINDING; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 1842366654     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:2<191::AID-CHIR21>3.0.CO;2-H     Document Type: Conference Paper

References (39)

1. Fringuelli, F., Taticchi, A. In: Dienes in the Diels-Alder Reaction. New York: John Wiley & Sons, Inc., 1990.
2. Rebiere, F., Riant, O, Kagan, H.B. Asymmetric Diels-Alder reaction catalysed by some chiral Lewis acids. Tetrahedron:Asymmetry 1:199-214, 1990.
3. Narasaka, K. Chiral Lewis acids in catalytic asymmetric reactions. Synthesis 1-11, 1991.
4. Seebach, D., Beck, A.K., Imwinkelned, R., Roggo, S., Wonnacott, A. Chirale Alkoxytitan(IV)-Komplexe für enantioselektive nucleophile Additionen an Aldehyde und als Lewis-Säuren in Diels-Alder-Reaktionen. Helv. Chim. Acta 70:954-974, 1987.
5. Irurre, J., Alonso-Alija, C., Piniella, J.F., Alvarez-Larena, A. Synthesis and structure of (4R, 5R)-α,α,α′,α′-2,2-Hexaphenyl-4,5-Dimethanol- 1,3-Dioxolane. Tetrahedron:Asymmetry 3:1591-1596, 1992.
6. (a) Narasaka, K., Yamamoto, I. Use of 1,3-oxazolidin-2-one derivatives of 3-borylpropenoic acids as β-hydroxy acrylic acid equivalents in the asymmetric Diels-Alder reaction catalyzed by chiral titanium reagent. Tetrahedron 48:5743-5754, 1992;
7. (b) Narasaka, K., Iwasawa, N., Inoue, M., Yamada, T., Nakashima, M., Sugimori, J. Asymmetric Diels-Alder reaction catalyzed by a chiral titanium reagent. J. Am. Chem. Soc. 111:5340-5345, 1989;
8. (c) Narasaka, K., Inoue, M., Okada, N. Asymmetric Diels-Alder reaction promoted by a chiral titanium reagent. Chem. Lett. 1109-1112, 1986.
9. Engler, T.A., Letavic, M.A., Lynch, K.O., Takusagawa, F. Formation and isolation of enantiomerically pure products in quantity from Diels-Alder reactions of 1,4-benzoquinones. J. Org. Chem. 59:11797-1183, 1994.
10. (a) Irurre, J., Alonso-Alija, C., Fernández-Serrat, A. (4R,5R)-α,α,α′,α′-2,2-hexaphenyl-4,5- dimethanol-1,3-dioxolane as chiral ligand of titanium in the Diels-Alder reaction: Application of the experimental design methodology and some considerations about the mechanism. Afinidad 51:413-418, 1994;
11. (b) Irurre, J., Tomás, X., Alonso-Alija, C., Carnicero, M.D. Síntesis de Diels-Alder asimétrica en presencia de un catalizador quiral de titanio. Aplicación de la metodología del diseño de experiencias. Afinidad 50:361-365, 1993.
12. Seebach, D., Beck, A.K., Schmidt, B., Wang, Y.M. Enantio- and diastereoselective titanium-TADDOLate catalyzed addition of diethyl and bis(3-Buten-1-yl) zinc to aldehydes. A full account with preparative details. Tetrahedron 50:4363-4384, 1994.
13. Narasaka, N., Hayashi, Y., Shimada, S. Asymmetric intramolecular ene reaction catalyzed by a chiral titanium alkoxide. Chem. Lett. 1609-1612, 1988.
14. Mikami, K., Terada, M., Nakai, T. Catalytic asymmetric glyoxylate-ene reaction: A practical access to α-hydroxy esters in high enantiomeric purities. J. Am. Chem. Soc. 112:3939-3954, 1990.
15. (a) Hayashi, Y., Niihata, S., Narasaka, K. [2+2] Cycloaddition reaction between allenyl sulfides and electron deficient olefines promoted by Lewis acids. Chem. Lett. 00:2091-2094, 1990;
16. (b) Hayashi, Y., Narasaka, K. Asymmetric [2+2] Cycloaddition reaction between α,β-unsaturated acid derivatives and alkynyl or alkenyl sulfides catalyzed by a chiral titanium reagent. Chem. Lett. 1295-1298, 1990.
17. Gothelf, K.V., Jørgensen, K.A. Transition-metal catalyzed asymmetric 1,3-dipolar cycloaddition reactions between alkenes and nitrones. J. Org. Chem. 59:5687-5691, 1994.
18. Minimikawa, H., Hayakawa, S., Yamada, T., Iwasawa, N., Narasaka, K. Asymmetric hydrocyanation of aldehydes using chiral titanium reagents. Bull. Chem. Soc. Jpn. 61:4379-4383, 1988.
19. Greeves, N., Pease, E., Bowden, M.C., Brown, S.M. Enantioselective addition of organocerium reagents to aldehydes: Effects of TADDOL ligand structure. Tetrahedron Lett. 37:2675-2678, 1996 (and the references cited herein).
20. Merrifield, R.B. Solid phase synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85:2149-2154, 1963.
21. Itsuno, S., Sakurai, Y., Ito, K., Maruyama, T., Nakahama, S., Fréchet, J.M.J. New solid-phase catalyst for asymmetric synthesis: Cross-linked polymers containing a chiral Schiff base-zinc complex. J. Org. Chem. 55:304-310, 1990.
22. Soai, K., Niwa, S., Watanabe, M. Polymer-bound N-alkylnorephedrines as efficient chiral catalyst for the enantioselective addition of dialkylzincs to both aromatic and aliphatic aldehydes. J. Chem. Soc., Perkin Trans. 1:109-113, 1989.
23. El Moualij, N., Caze, C. Enantioselective addition of diethylzinc to aldehydes catalysed by polymer supported chiral oxazaborolidine. Eur. Polym. J. 31:193-198, 1995.
24. (a) Adjidjonou, K., Caze, C. Asymmetric reduction of acetophenone with chiral polymeric reagents: Supported sodium borohydride on chiral amino-alcohol bound to a polymer. Eur. Polym. J. 31:749-754, 1995;
25. (b) Caze, C., El Moualij, N., Hodge, P., Lock, C.J., Ma, J. Some enantioselective borane reductions of prochiral ketones catalysed by polymer-supported oxazaborolidines bound via the Boron atom. J. Chem. Soc. Perkin Trans. 1:345-349, 1995;
26. (c) Caze, C. Asymmetric reduction of prochiral ketones using polymer-supported catalyst and reagents. React. Funct. Polymers 26:85-94, 1995.
27. Farrall, M.J., Alexis, M., Trecarten, M. Polymer-bound chiral tartrate esters for the asymmetric epoxidation of allylic alcohols. I. Nouveau J. Chim. 7:449-451, 1983.
28. (a) Kamahori, K., Shoichi, T., Ito, K., Itsuno, S. Synthesis of polymer-supported chiral N-sulfonylamino acids and their use in asymmetric Diels-Alder reaction of cyclopentadiene with methacrolein. Tetrahedron:Asymmetry 6:2547-2555, 1995.
29. (b) Itsuno, S., Watanabe, K., Koizumi, T., Ito, K. Asymmetric Diels-Alder reaction of cyclopentadiene with methacrolein using polymer-supported chiral catalyst. React. Polymers 24:219-227, 1995;
30. (c) Itsuno, S., Kamahori, K., Watanabe, K., Ito, K. Polymer-supported chiral Lewis acids as asymmetric catalysts for Diels-Alder reactions of methacrolein with cyclopentadiene. Tetrahedron:Asymmetry 5:523-526, 1994.
31. Tatchell, A.R., Smith, P.W.G., Rogers, V., Hannaford, A.J., Furniss, B.S. In: Vogel's Textbook of Practical Organic Chemistry. New York: Longman, Inc., 1989: 395-412.
32. Seebach, D., Weidmann, B., Widler, L. Titanium and zirconium derivatives in organic synthesis. In: Modern Synthetic Methods 1983. Aarau, Switzerland: R. Scheffold, 3:217-353, 1983.
33. 7). Spectrochim. Acta, A 24:1213-1217, 1968.
34. Evans, D.A., Chapman, K.T., Bisaha, J. Asymmetric Diels-Alder cycloaddition reactions of chiral α,β-unsaturated-N-acyloxazolidinones. J. Am. Chem. Soc. 110:1238-1256, 1988.
35. Frechet, J.M., Schuerch, C. Solid-phase synthesis of oligosaccharides. I. Preparation of the solid support. Poly[p-(1-propren-3-ol-1-yl)styrene]. J. Am. Chem. Soc. 93:492-495, 1971.
36. Altava, B., Burguete, M.I., Luis, S.V., Mayoral, J.A. Functionalization of polystyrene resins with chiral fragments derived from tartaric acid. Tetrahedron 50:7535-7542, 1994.
37. Harrison, C.R., Hodge, P., Kemp, J., Perry, G.M. Introduction of carboxyl groups into crosslinked polystyrene. Makromol. Chem. 176:267-274, 1975.
38. Fréchet, J.M.J. Synthesis and applications of organic polymers as supports and protecting groups. Tetrahedron 37:663-683, 1981.
39. Luis, S.V., Burguete, M.I., Ramirez, N., Mayoral, J.A., Cativiela, C., Royo, A.J. Polymer-supported Ti and Al Lewis acids as catalysts in Diels-Alder reactions. React. Polymers 18:237-248, 1992.