SCOPUS 정보 검색 플랫폼

Chemistry - A European Journal

Volumn 9, Issue 14, 2003, Pages 3270-3281

Development of the traceless phenylhydrazide linker for solid-phase synthesis

(3) Stieber, Frank a,b Grether, Uwe a,b Waldmann, Herbert a,b

a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY (Germany)

b TU DORTMUND UNIVERSITY (Germany)

Author keywords

Combinatorial chemistry; Phenylhydrazides; Solid phase synthesis; Traceless linker

Indexed keywords

CARBOXYLIC ACIDS; CHEMICAL ACTIVATION; CHEMICAL BONDS; HYDRAZINE; OXIDATION; REACTION KINETICS; RESINS; SEPARATION; SYNTHESIS (CHEMICAL);

GRIGNARD REACTION;

AROMATIC COMPOUNDS;

CARBOXYLIC ACID DERIVATIVE; HYDRAZIDE DERIVATIVE; IMIDE; METHANOL; N BROMOSUCCINIMIDE; PHENYLHYDRAZINE DERIVATIVE; POLYMER; REAGENT; RESIN;

ARTICLE; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; OXIDATION; REACTION ANALYSIS; SOLID; SYNTHESIS;

EID: 0041591464 PISSN: 09476539 EISSN: None Source Type: Journal
DOI: 10.1002/chem.200304820 Document Type: Article

Times cited : (30)

References (70)

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7
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- For the development of traceless linkers see, for example: a) F. X. Woolard, J. Paetsch, J. A. Ellman, J. Org. Chem. 1997, 62, 6102-6103; b) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1997, 62, 2885-2893, and references therein; c) K. A. Newlander, B. Chenera, D. F. Veber, N. C. F. Yim, M. L. Moore, J. Org. Chem. 1997, 62, 6726-6732, and references therein; d) M. Schuster, N. Lucas, S. Blechert, Chem. Commun. 1997, 823-824; e) T. L. Boehm, H. D. H. Showalter, J. Org. Chem. 1996, 61, 6498-6499; f) Y. Han, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 2703-2706; g) K. W. Jung, X. Y. Zhao, K. D. Janda, Tetrahedron 1997, 53, 6645-6652, and references therein; h) T. Ruhland, K. Andersen, H. Pedersen, J. Org. Chem. 1998, 63, 9204-9211; i) K. C. Nicolaou, J. Pastor, S. Barluenga, N. Winssinger, Chem. Commun. 1998, 1947-1948; j) S. Bräse, D. Enders, J. Köbberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3413-3415; k) F. Zaragoza, Tetrahedron Lett. 1997, 38, 7291-7294; l) P. Garibay, J. Nielsen, T. Hoeg-Jensen, Tetrahedron Lett. 1998, 39, 2207-2210; m) M. M. Sim, C. L. Lee, A. Ganesan, Tetrahedron Lett. 1998, 39, 6399-6402; n) S. Jin, D. P. Holub, D. J. Wustrow, Tetrahedron Lett. 1998, 39, 3651-3654; for reviews summarizing recent developments, see: o) S. Bräse, S. Dahmen, Chem. Eur. J. 2000, 6, 1899-1905; p) A. C. Comely, S. E. Gibson, Angew. Chem. 2001, 113, 1042-1063; Angew. Chem. Int. Ed. 2001, 40, 1012-1032.
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- Schuster, M.¹ Lucas, N.² Blechert, S.³

8
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- For the development of traceless linkers see, for example: a) F. X. Woolard, J. Paetsch, J. A. Ellman, J. Org. Chem. 1997, 62, 6102-6103; b) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1997, 62, 2885-2893, and references therein; c) K. A. Newlander, B. Chenera, D. F. Veber, N. C. F. Yim, M. L. Moore, J. Org. Chem. 1997, 62, 6726-6732, and references therein; d) M. Schuster, N. Lucas, S. Blechert, Chem. Commun. 1997, 823-824; e) T. L. Boehm, H. D. H. Showalter, J. Org. Chem. 1996, 61, 6498-6499; f) Y. Han, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 2703-2706; g) K. W. Jung, X. Y. Zhao, K. D. Janda, Tetrahedron 1997, 53, 6645-6652, and references therein; h) T. Ruhland, K. Andersen, H. Pedersen, J. Org. Chem. 1998, 63, 9204-9211; i) K. C. Nicolaou, J. Pastor, S. Barluenga, N. Winssinger, Chem. Commun. 1998, 1947-1948; j) S. Bräse, D. Enders, J. Köbberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3413-3415; k) F. Zaragoza, Tetrahedron Lett. 1997, 38, 7291-7294; l) P. Garibay, J. Nielsen, T. Hoeg-Jensen, Tetrahedron Lett. 1998, 39, 2207-2210; m) M. M. Sim, C. L. Lee, A. Ganesan, Tetrahedron Lett. 1998, 39, 6399-6402; n) S. Jin, D. P. Holub, D. J. Wustrow, Tetrahedron Lett. 1998, 39, 3651-3654; for reviews summarizing recent developments, see: o) S. Bräse, S. Dahmen, Chem. Eur. J. 2000, 6, 1899-1905; p) A. C. Comely, S. E. Gibson, Angew. Chem. 2001, 113, 1042-1063; Angew. Chem. Int. Ed. 2001, 40, 1012-1032.
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9
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10
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- Ruhland, T.¹ Andersen, K.² Pedersen, H.³

12
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- For the development of traceless linkers see, for example: a) F. X. Woolard, J. Paetsch, J. A. Ellman, J. Org. Chem. 1997, 62, 6102-6103; b) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1997, 62, 2885-2893, and references therein; c) K. A. Newlander, B. Chenera, D. F. Veber, N. C. F. Yim, M. L. Moore, J. Org. Chem. 1997, 62, 6726-6732, and references therein; d) M. Schuster, N. Lucas, S. Blechert, Chem. Commun. 1997, 823-824; e) T. L. Boehm, H. D. H. Showalter, J. Org. Chem. 1996, 61, 6498-6499; f) Y. Han, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 2703-2706; g) K. W. Jung, X. Y. Zhao, K. D. Janda, Tetrahedron 1997, 53, 6645-6652, and references therein; h) T. Ruhland, K. Andersen, H. Pedersen, J. Org. Chem. 1998, 63, 9204-9211; i) K. C. Nicolaou, J. Pastor, S. Barluenga, N. Winssinger, Chem. Commun. 1998, 1947-1948; j) S. Bräse, D. Enders, J. Köbberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3413-3415; k) F. Zaragoza, Tetrahedron Lett. 1997, 38, 7291-7294; l) P. Garibay, J. Nielsen, T. Hoeg-Jensen, Tetrahedron Lett. 1998, 39, 2207-2210; m) M. M. Sim, C. L. Lee, A. Ganesan, Tetrahedron Lett. 1998, 39, 6399-6402; n) S. Jin, D. P. Holub, D. J. Wustrow, Tetrahedron Lett. 1998, 39, 3651-3654; for reviews summarizing recent developments, see: o) S. Bräse, S. Dahmen, Chem. Eur. J. 2000, 6, 1899-1905; p) A. C. Comely, S. E. Gibson, Angew. Chem. 2001, 113, 1042-1063; Angew. Chem. Int. Ed. 2001, 40, 1012-1032.
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13
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- For the development of traceless linkers see, for example: a) F. X. Woolard, J. Paetsch, J. A. Ellman, J. Org. Chem. 1997, 62, 6102-6103; b) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1997, 62, 2885-2893, and references therein; c) K. A. Newlander, B. Chenera, D. F. Veber, N. C. F. Yim, M. L. Moore, J. Org. Chem. 1997, 62, 6726-6732, and references therein; d) M. Schuster, N. Lucas, S. Blechert, Chem. Commun. 1997, 823-824; e) T. L. Boehm, H. D. H. Showalter, J. Org. Chem. 1996, 61, 6498-6499; f) Y. Han, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 2703-2706; g) K. W. Jung, X. Y. Zhao, K. D. Janda, Tetrahedron 1997, 53, 6645-6652, and references therein; h) T. Ruhland, K. Andersen, H. Pedersen, J. Org. Chem. 1998, 63, 9204-9211; i) K. C. Nicolaou, J. Pastor, S. Barluenga, N. Winssinger, Chem. Commun. 1998, 1947-1948; j) S. Bräse, D. Enders, J. Köbberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3413-3415; k) F. Zaragoza, Tetrahedron Lett. 1997, 38, 7291-7294; l) P. Garibay, J. Nielsen, T. Hoeg-Jensen, Tetrahedron Lett. 1998, 39, 2207-2210; m) M. M. Sim, C. L. Lee, A. Ganesan, Tetrahedron Lett. 1998, 39, 6399-6402; n) S. Jin, D. P. Holub, D. J. Wustrow, Tetrahedron Lett. 1998, 39, 3651-3654; for reviews summarizing recent developments, see: o) S. Bräse, S. Dahmen, Chem. Eur. J. 2000, 6, 1899-1905; p) A. C. Comely, S. E. Gibson, Angew. Chem. 2001, 113, 1042-1063; Angew. Chem. Int. Ed. 2001, 40, 1012-1032.
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14
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- (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3413-3415

15
- 0030722306
- For the development of traceless linkers see, for example: a) F. X. Woolard, J. Paetsch, J. A. Ellman, J. Org. Chem. 1997, 62, 6102-6103; b) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1997, 62, 2885-2893, and references therein; c) K. A. Newlander, B. Chenera, D. F. Veber, N. C. F. Yim, M. L. Moore, J. Org. Chem. 1997, 62, 6726-6732, and references therein; d) M. Schuster, N. Lucas, S. Blechert, Chem. Commun. 1997, 823-824; e) T. L. Boehm, H. D. H. Showalter, J. Org. Chem. 1996, 61, 6498-6499; f) Y. Han, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 2703-2706; g) K. W. Jung, X. Y. Zhao, K. D. Janda, Tetrahedron 1997, 53, 6645-6652, and references therein; h) T. Ruhland, K. Andersen, H. Pedersen, J. Org. Chem. 1998, 63, 9204-9211; i) K. C. Nicolaou, J. Pastor, S. Barluenga, N. Winssinger, Chem. Commun. 1998, 1947-1948; j) S. Bräse, D. Enders, J. Köbberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3413-3415; k) F. Zaragoza, Tetrahedron Lett. 1997, 38, 7291-7294; l) P. Garibay, J. Nielsen, T. Hoeg-Jensen, Tetrahedron Lett. 1998, 39, 2207-2210; m) M. M. Sim, C. L. Lee, A. Ganesan, Tetrahedron Lett. 1998, 39, 6399-6402; n) S. Jin, D. P. Holub, D. J. Wustrow, Tetrahedron Lett. 1998, 39, 3651-3654; for reviews summarizing recent developments, see: o) S. Bräse, S. Dahmen, Chem. Eur. J. 2000, 6, 1899-1905; p) A. C. Comely, S. E. Gibson, Angew. Chem. 2001, 113, 1042-1063; Angew. Chem. Int. Ed. 2001, 40, 1012-1032.
- (1997) Tetrahedron Lett. , vol.38 , pp. 7291-7294
- Zaragoza, F.¹

16
- 0032499144
- For the development of traceless linkers see, for example: a) F. X. Woolard, J. Paetsch, J. A. Ellman, J. Org. Chem. 1997, 62, 6102-6103; b) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1997, 62, 2885-2893, and references therein; c) K. A. Newlander, B. Chenera, D. F. Veber, N. C. F. Yim, M. L. Moore, J. Org. Chem. 1997, 62, 6726-6732, and references therein; d) M. Schuster, N. Lucas, S. Blechert, Chem. Commun. 1997, 823-824; e) T. L. Boehm, H. D. H. Showalter, J. Org. Chem. 1996, 61, 6498-6499; f) Y. Han, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 2703-2706; g) K. W. Jung, X. Y. Zhao, K. D. Janda, Tetrahedron 1997, 53, 6645-6652, and references therein; h) T. Ruhland, K. Andersen, H. Pedersen, J. Org. Chem. 1998, 63, 9204-9211; i) K. C. Nicolaou, J. Pastor, S. Barluenga, N. Winssinger, Chem. Commun. 1998, 1947-1948; j) S. Bräse, D. Enders, J. Köbberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3413-3415; k) F. Zaragoza, Tetrahedron Lett. 1997, 38, 7291-7294; l) P. Garibay, J. Nielsen, T. Hoeg-Jensen, Tetrahedron Lett. 1998, 39, 2207-2210; m) M. M. Sim, C. L. Lee, A. Ganesan, Tetrahedron Lett. 1998, 39, 6399-6402; n) S. Jin, D. P. Holub, D. J. Wustrow, Tetrahedron Lett. 1998, 39, 3651-3654; for reviews summarizing recent developments, see: o) S. Bräse, S. Dahmen, Chem. Eur. J. 2000, 6, 1899-1905; p) A. C. Comely, S. E. Gibson, Angew. Chem. 2001, 113, 1042-1063; Angew. Chem. Int. Ed. 2001, 40, 1012-1032.
- (1998) Tetrahedron Lett. , vol.39 , pp. 2207-2210
- Garibay, P.¹ Nielsen, J.² Hoeg-Jensen, T.³

17
- 0032572876
- For the development of traceless linkers see, for example: a) F. X. Woolard, J. Paetsch, J. A. Ellman, J. Org. Chem. 1997, 62, 6102-6103; b) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1997, 62, 2885-2893, and references therein; c) K. A. Newlander, B. Chenera, D. F. Veber, N. C. F. Yim, M. L. Moore, J. Org. Chem. 1997, 62, 6726-6732, and references therein; d) M. Schuster, N. Lucas, S. Blechert, Chem. Commun. 1997, 823-824; e) T. L. Boehm, H. D. H. Showalter, J. Org. Chem. 1996, 61, 6498-6499; f) Y. Han, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 2703-2706; g) K. W. Jung, X. Y. Zhao, K. D. Janda, Tetrahedron 1997, 53, 6645-6652, and references therein; h) T. Ruhland, K. Andersen, H. Pedersen, J. Org. Chem. 1998, 63, 9204-9211; i) K. C. Nicolaou, J. Pastor, S. Barluenga, N. Winssinger, Chem. Commun. 1998, 1947-1948; j) S. Bräse, D. Enders, J. Köbberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3413-3415; k) F. Zaragoza, Tetrahedron Lett. 1997, 38, 7291-7294; l) P. Garibay, J. Nielsen, T. Hoeg-Jensen, Tetrahedron Lett. 1998, 39, 2207-2210; m) M. M. Sim, C. L. Lee, A. Ganesan, Tetrahedron Lett. 1998, 39, 6399-6402; n) S. Jin, D. P. Holub, D. J. Wustrow, Tetrahedron Lett. 1998, 39, 3651-3654; for reviews summarizing recent developments, see: o) S. Bräse, S. Dahmen, Chem. Eur. J. 2000, 6, 1899-1905; p) A. C. Comely, S. E. Gibson, Angew. Chem. 2001, 113, 1042-1063; Angew. Chem. Int. Ed. 2001, 40, 1012-1032.
- (1998) Tetrahedron Lett. , vol.39 , pp. 6399-6402
- Sim, M.M.¹ Lee, C.L.² Ganesan, A.³

18
- 0032575176
- For the development of traceless linkers see, for example: a) F. X. Woolard, J. Paetsch, J. A. Ellman, J. Org. Chem. 1997, 62, 6102-6103; b) M. J. Plunkett, J. A. Ellman, J. Org. Chem. 1997, 62, 2885-2893, and references therein; c) K. A. Newlander, B. Chenera, D. F. Veber, N. C. F. Yim, M. L. Moore, J. Org. Chem. 1997, 62, 6726-6732, and references therein; d) M. Schuster, N. Lucas, S. Blechert, Chem. Commun. 1997, 823-824; e) T. L. Boehm, H. D. H. Showalter, J. Org. Chem. 1996, 61, 6498-6499; f) Y. Han, S. D. Walker, R. N. Young, Tetrahedron Lett. 1996, 37, 2703-2706; g) K. W. Jung, X. Y. Zhao, K. D. Janda, Tetrahedron 1997, 53, 6645-6652, and references therein; h) T. Ruhland, K. Andersen, H. Pedersen, J. Org. Chem. 1998, 63, 9204-9211; i) K. C. Nicolaou, J. Pastor, S. Barluenga, N. Winssinger, Chem. Commun. 1998, 1947-1948; j) S. Bräse, D. Enders, J. Köbberling, F. Avemaria, Angew. Chem. 1998, 110, 3614-3616; Angew. Chem. Int. Ed. 1998, 37, 3413-3415; k) F. Zaragoza, Tetrahedron Lett. 1997, 38, 7291-7294; l) P. Garibay, J. Nielsen, T. Hoeg-Jensen, Tetrahedron Lett. 1998, 39, 2207-2210; m) M. M. Sim, C. L. Lee, A. Ganesan, Tetrahedron Lett. 1998, 39, 6399-6402; n) S. Jin, D. P. Holub, D. J. Wustrow, Tetrahedron Lett. 1998, 39, 3651-3654; for reviews summarizing recent developments, see: o) S. Bräse, S. Dahmen, Chem. Eur. J. 2000, 6, 1899-1905; p) A. C. Comely, S. E. Gibson, Angew. Chem. 2001, 113, 1042-1063; Angew. Chem. Int. Ed. 2001, 40, 1012-1032.
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- Jin, S.¹ Holub, D.P.² Wustrow, D.J.³

19
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20
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