Synthesis and preliminary studies on a novel class of soluble amino alcohol reagents based on methacrylate copolymers

Tetrahedron

Volumn 59, Issue 31, 2003, Pages 5823-5830

  Edwards, Christopher W ^a   Haddleton, David M ^a   Morsley, David ^a   Shipton, Mark R ^b   Wills, Martin ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Asymmetric; Catalyst; Dialkylzinc; Ligand; Soluble polymers

Indexed keywords

2 (4' ANISYLBENZYLMETHYLAMINO) 1 PHENYL[(TERT BUTYLDIMETHYLSILYL)OXY]PROPANE; 2 (4' PHENYLBENZYLMETHYLAMINO) 1 PHENYL[(TERT BUTYLDIMETHYLSILYL)OXY]PROPANE; AMINOALCOHOL; COPOLYMER; DIETHYLZINC; METHACRYLIC ACID DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY; SYNTHESIS;

EID: 0037769866     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00975-X     Document Type: Article

References (42)

1. (a) Noyori R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. (b) Ojima I. Catalytic Asymmetric Synthesis; VCH: Berlin, 1993.
3. (c) Jacobsen E.N.; Pfaltz A.; Yamamoto H. Handbook of Asymmetric Catalysis; Springer: Heidelberg, 1999.
4. (a) Blaser H.-U. Tetrahedron Asymmetry 1991, 2, 843-866.
5. (b) Minder B.; Schurch M.; Mallat T.; Baiker A.; Heinz T.; Pfaltz A. J. Catal. 1996, 160, 261-268.
6. (c) Wang J.; Sun Y.; LeBlond C.; Landau R.N.; Blackmond D.G. J. Catal. 1996, 161, 752-758.
7. (d) Studer M.; Blaser H.-U.; Exner C. Adv. Synth. Catal. 2003, 345, 45-65.
8. (e) Blaser H.-U. Chem. Commun. 2003, 293-296.
9. de Miguel Y.R., Brule E., Margue R.G. J. Chem. Soc., Perkin Trans. 1. 2001;3085-3094.
10. (a) Toy P.H.; Reger T.S.; Janda K.D. Aldrichemica Acta. 2000, 33, 87-93.
11. (b) Sherrington D.C. Chem. Commun. 1998, 2275-2286.
12. (c) Shuttleworth S.J.; Allin S.M.; Sharma P.K. Synthesis 1997, 1217-1239.
13. (d) Hodge P. Chem. Soc. Rev. 1997, 26, 417-424.
14. (e) Li W.; Yan B. J. Org. Chem. 1998, 63, 4092-4097.
15. (f) Canali L.; Cowan E.; Deleuze H.; Gibson C.L.; Sherrington D.C. Chem. Commun. 1998, 2561-2562.
16. (a) Dickerson T.J.; Reed N.N.; Janda K.D. Chem. Rev. 2002, 102, 3325-3343.
17. (b) Wentworth P. Jr.; Vandersteen A.M.; Janda K.D. Chem. Commun. 1997, 759-760.
18. (c) Han H.; Janda K.D. Tetrahedron Lett. 1997, 38, 1527-1530.
19. (d) Han H.; Janda K.D. J. Am. Chem. Soc. 1996, 118, 7632-7633.
20. (e) Hovestad N.J.; Eggeling E.B.; Heidbuchel H.J.; Jastrzebski J.T.B.H.; Kragl U.; Keim W.; Vogt D.; van Koten G. Angew. Chem. Int. Ed. 1999, 38, 1655-1658.
21. (f) de Groo D.; Eggeling E.B.; de Wilde J.C.; Kooijman H.; van Haaren R.J.; van der Made A.W.; Spek A.L.; Vogt D.; Reek J.N.H.; Kamer P.C.J.; van Leeuwen P.W.N.M. Chem. Commun. 1999, 1623-1624.
22. (a) Haddleton D.M.; Morsley D.R.; O'Donnell J.P.; Richards S.N. J. Polym. Sci., Part A Polym. Chem. 1999, 37, 3549-3557.
23. (b) Bon S.A.F.; Morsley D.R.; Waterson J.; Haddleton D.M.; Lees M.R.; Horne T. Macromol. Symp. 2001, 165, 29-41.
24. (a) Hodge P., Monvisade P., Morris G.A., Preece I. Chem. Commun. 2001;239-240
25. (b) Bergbreiter D.E., Osburn P.L., Wilson A., Sink E.M. J. Am. Chem. Soc. 122:2000;9058-9064
26. (c) Bergbreiter D.E. Chem. Rev. 102:2002;3345-3383
27. (d) Osburn P.L., Bergbreiter D.E. Prog. Polym. Sci. 26:2001;2015-2081
28. (e) Bergbreiter D.E., Liu Y.-S. Tetrahedron Lett. 38:1997;7843-7846
29. (f) Bergbreiter D.E., Liu Y.-S. Tetrahedron Lett. 38:1997;3703-3706.
30. Soai K., Niwa S. Chem. Rev. 92:1992;833-856.
31. (a) Sung D.W.L., Hodge P., Stratford P.W. J. Chem. Soc., Perkin Trans. 1. 1999;1463-1472
32. (b) Itsuno S., Frechet J.M.J. J. Org. Chem. 52:1987;4140-4142
33. (c) Itsuno S., Sakurai Y., Ito K., Maruyama T., Nakahama S., Frechet J.M.J. J. Org. Chem. 55:1990;304-310
34. (d) Vidal-Ferran A., Bampos N., Moyano A., Pericas M.A., Riera A., Sanders J.K.M. J. Org. Chem. 63:1998;6309-6318
35. (e) Hu Q.-S., Sun C., Monaghan C.E. Tetrahedron Lett. 42:2001;7725-7728
36. (f) Hu Q.-S., Huang W.-S., Vitharana D., Zheng X.-F., Pu L. J. Am. Chem. Soc. 119:1997;12454-12464.
37. Hassan J., Sevignon M., Gozzi C., Schulz E., Lemaire M. Chem. Rev. 102:2002;1359-1469.
38. Kawamoto A.M., Wills M. J. Chem. Soc., Perkin Trans. 1. 2001;1916-1928.
39. Brussee J., van Benthem R.A.T.M., Kruse C.G., Gen A. Tetrahedron Asymmetry. 1:1990;163-166.
40. Badone D., Barone M., Cardamone R., Ielmini A., Guzzi U. J. Org. Chem. 62:1997;7170-7173.
41. Giroux A., Han Y.X., Prasit P. Tetrahedron Lett. 38:1997;3841-3844.
42. Fletcher D.A., McMeeking R.F., Parkin D. J. Chem. Inf. Comput. Sci. 36:1996;746-749.