New scavenger resin for the reversible linking and monoprotection of functionalized aromatic aldehydes

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3921-3924

  Zhu, Mingzhao ^a   Ruijter, Eelco ^a   Wessjohann, Ludger A ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; RIFAMPICIN;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ORGANIC CHEMISTRY; SOLID;

EID: 8744236005     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048610h     Document Type: Article

References (50)

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11. In preceding studies with various commercial resins and linkers, including polystyrene-based sulfonylhydrazine resins, we were unsuccessful in performing enzymatic and organometallic reactions of resin-bound substrates in sufficient yield or quality. (Cf. our recent study of Cr(II)-mediated reactions with SPOC: Wessjohann, L. A.; Wild, H.; Schrekker, H. S. Tetrahedron Lett. 2004, in print.)
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20. Some recent examples: (a) Barkley, A.; Arya, P. Chem. Eur. J. 2001, 7, 555-563. (b) Wu, C. W.; Sanborn, T. J.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2001, 123, 2958-2963. (c) Melnyk, O.; Fruchart, J.-S.; Grandjean, C.; Gras-Masse, H. J. Org. Chem. 2001, 66, 4153-4160. (d) Kohli, R. M.; Walsh, C. T.; Burkart, M. D. Nature 2002, 418, 658-661. (e) Pastor, J. J.; Fernández, I.; Rabanal, P.; Giralt, E. Org. Lett. 2002, 4, 3831-3833. (f) Ulijn, R. V.; Baragana, B.; Halling, P. J.; Flitsch, S. L. J. Am. Chem. Soc. 2002, 124, 10988-10989.
21. Some recent examples: (a) Barkley, A.; Arya, P. Chem. Eur. J. 2001, 7, 555-563. (b) Wu, C. W.; Sanborn, T. J.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2001, 123, 2958-2963. (c) Melnyk, O.; Fruchart, J.-S.; Grandjean, C.; Gras-Masse, H. J. Org. Chem. 2001, 66, 4153-4160. (d) Kohli, R. M.; Walsh, C. T.; Burkart, M. D. Nature 2002, 418, 658-661. (e) Pastor, J. J.; Fernández, I.; Rabanal, P.; Giralt, E. Org. Lett. 2002, 4, 3831-3833. (f) Ulijn, R. V.; Baragana, B.; Halling, P. J.; Flitsch, S. L. J. Am. Chem. Soc. 2002, 124, 10988-10989.
22. Some recent examples: (a) Barkley, A.; Arya, P. Chem. Eur. J. 2001, 7, 555-563. (b) Wu, C. W.; Sanborn, T. J.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2001, 123, 2958-2963. (c) Melnyk, O.; Fruchart, J.-S.; Grandjean, C.; Gras-Masse, H. J. Org. Chem. 2001, 66, 4153-4160. (d) Kohli, R. M.; Walsh, C. T.; Burkart, M. D. Nature 2002, 418, 658-661. (e) Pastor, J. J.; Fernández, I.; Rabanal, P.; Giralt, E. Org. Lett. 2002, 4, 3831-3833. (f) Ulijn, R. V.; Baragana, B.; Halling, P. J.; Flitsch, S. L. J. Am. Chem. Soc. 2002, 124, 10988-10989.
23. Some recent examples: (a) Barkley, A.; Arya, P. Chem. Eur. J. 2001, 7, 555-563. (b) Wu, C. W.; Sanborn, T. J.; Zuckermann, R. N.; Barron, A. E. J. Am. Chem. Soc. 2001, 123, 2958-2963. (c) Melnyk, O.; Fruchart, J.-S.; Grandjean, C.; Gras-Masse, H. J. Org. Chem. 2001, 66, 4153-4160. (d) Kohli, R. M.; Walsh, C. T.; Burkart, M. D. Nature 2002, 418, 658-661. (e) Pastor, J. J.; Fernández, I.; Rabanal, P.; Giralt, E. Org. Lett. 2002, 4, 3831-3833. (f) Ulijn, R. V.; Baragana, B.; Halling, P. J.; Flitsch, S. L. J. Am. Chem. Soc. 2002, 124, 10988-10989.
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27. Selected examples for acetal linkers: (a) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182. (b) Metz, W. A.; Jones, W. D.; Ciske, F. L.; Peet, N. P. Bioorg. Med. Chem. Lett. 1998, 8, 2399-2402. (c) Ede, N. J.; Bray, A. M. Tetrahedron Lett. 1997, 38, 7119-7122. (d) Bertini, V.; Lucchesini, F.; Pocci, M.; De Munno, A. Tetrahedron Lett. 1998, 39, 9263-9266. (e) Wong, J. Y.; Leznoff, C. C. Can. J. Chem. 1973, 51, 3756-3764.
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29. Selected examples for acetal linkers: (a) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182. (b) Metz, W. A.; Jones, W. D.; Ciske, F. L.; Peet, N. P. Bioorg. Med. Chem. Lett. 1998, 8, 2399-2402. (c) Ede, N. J.; Bray, A. M. Tetrahedron Lett. 1997, 38, 7119-7122. (d) Bertini, V.; Lucchesini, F.; Pocci, M.; De Munno, A. Tetrahedron Lett. 1998, 39, 9263-9266. (e) Wong, J. Y.; Leznoff, C. C. Can. J. Chem. 1973, 51, 3756-3764.
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