A novel strategy for the solid-phase synthesis of substituted indolines [12]

Journal of the American Chemical Society

Volumn 122, Issue 12, 2000, Pages 2966-2967

  Nicolaou, K C ^a   Roecker, A J ^a   Pfefferkorn, Jeffrey A ^a   Cao, Gou Qiang ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

CATALYSIS; CYCLIZATION; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034728665     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994373f     Document Type: Letter

References (21)

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13. To our best knowledge, this is the first example whereby radical cleavage from a solid support is accompanied by subsequent intramolecular cyclization to afford an additional ring system in the target molecule. Solid-phase non-releasing radical cyclizations have been described previously; for examples, see: (a) Du, X.; Armstrong, R. W. J. Org. Chem. 1997, 62, 5678-5679. (b) Watanabe, Y.; Ishikawa, S.; Takao, G.; Toru, T. Tetrahedron Lett. 1999, 40, 3411-3414. In addition, traceless radical cleavages of selenium resins have been described, see references 4a-c.
14. To our best knowledge, this is the first example whereby radical cleavage from a solid support is accompanied by subsequent intramolecular cyclization to afford an additional ring system in the target molecule. Solid- phase non-releasing radical cyclizations have been described previously; for examples, see: (a) Du, X.; Armstrong, R. W. J. Org. Chem. 1997, 62, 5678- 5679. (b) Watanabe, Y.; Ishikawa, S.; Takao, G.; Toru, T. Tetrahedron Lett. 1999, 40, 3411-3414. In addition, traceless radical cleavages of selenium resins have been described, see references 4a-c.
15. For a previous method for the solid-phase synthesis of indolines, see: Wang, Y.; Huang, T.-N. Tetrahedron Lett. 1998, 39, 9605-9608.
16. For solution-phase precedent, see: (a) Clive, D. L. J.; Wong, C. K.; Kiel, W. A.; Menchen, S. M. J. C. S. Chem. Commun. 1978, 379-380. (b) Clive D. L. J.; Farina, V.; Singh, A.; Wong, C. K.; Kiel, W. A.; Menchen, S. M. J. Org. Chem. 1980, 45, 2120-2126. (c) Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, S. J.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 3891-3898.
17. For solution-phase precedent, see: (a) Clive, D. L. J.; Wong, C. K.; Kiel, W. A.; Menchen, S. M. J. C. S. Chem. Commun. 1978, 379-380. (b) Clive D. L. J.; Farina, V.; Singh, A.; Wong, C. K.; Kiel, W. A.; Menchen, S. M. J. Org. Chem. 1980, 45, 2120-2126. (c) Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, S. J.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 3891-3898.
18. For solution-phase precedent, see: (a) Clive, D. L. J.; Wong, C. K.; Kiel, W. A.; Menchen, S. M. J. C. S. Chem. Commun. 1978, 379-380. (b) Clive D. L. J.; Farina, V.; Singh, A.; Wong, C. K.; Kiel, W. A.; Menchen, S. M. J. Org. Chem. 1980, 45, 2120-2126. (c) Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, S. J.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 3891-3898.
19. Separation of the desired indoline cleavage products from organotin byproducts represents an obstacle to the combinatorial use of this methodology. The polarity-based purification used here relies on the desired product being prontonated and taken into the aqueous phase such that the organotin species can be removed with the organic phase. For a review of other applicable methods, see: Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174-1196.
20. 9 purification.
21. See Supporting Information for preparation of o-allyl anilines.