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Volumn 11, Issue 11, 2009, Pages 2365-2368

Cu(I)-catalyzed diamination of disubstituted terminal olefins: An approach to potent NK 1 antagonist

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE; COPPER; DI TERT BUTYLDIAZIRIDINONE; DI-TERT-BUTYLDIAZIRIDINONE; IMIDAZOLE DERIVATIVE; NEUROKININ 1 RECEPTOR; NITROGEN; SCH 425078;

EID: 66149172045     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900808z     Document Type: Article
Times cited : (55)

References (58)
  • 5
    • 66149171394 scopus 로고    scopus 로고
    • For examples of metal-mediated diaminations, see the following. Tl: Aranda, V. G, Barluenga, J, Aznar, F. Synthesis 1974, 504. Os
    • For examples of metal-mediated diaminations, see the following. Tl: Aranda, V. G.; Barluenga, J.; Aznar, F. Synthesis 1974, 504. Os:
  • 8
    • 0000748578 scopus 로고    scopus 로고
    • Bäckvall, J.-E. Tetrahedron Lett. 1978, 163. Hg:
    • Bäckvall, J.-E. Tetrahedron Lett. 1978, 163. Hg:
  • 12
    • 23844527400 scopus 로고    scopus 로고
    • For a recent Cu(II)-mediated intramolecular diamination, see: Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250.
    • For a recent Cu(II)-mediated intramolecular diamination, see: Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250.
  • 14
    • 27144440348 scopus 로고    scopus 로고
    • For recent Pd(II)-and Ni(II)-catalyzed intramolecular diamination of olefins, see: Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586.
    • For recent Pd(II)-and Ni(II)-catalyzed intramolecular diamination of olefins, see: Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586.
  • 19
    • 0035915127 scopus 로고    scopus 로고
    • For Rh(II)-and Fe(III)-catalyzed diamination with TsNCl2, see: Li, G.; Wei, H.-X.; Kim, S. H.; Carducci, M. D. Angew. Chem., Int. Ed.2001, 40, 4277.
    • For Rh(II)-and Fe(III)-catalyzed diamination with TsNCl2, see: Li, G.; Wei, H.-X.; Kim, S. H.; Carducci, M. D. Angew. Chem., Int. Ed.2001, 40, 4277.
  • 21
    • 19744362485 scopus 로고    scopus 로고
    • For a recent Pd(II)-catalyzed intermolecular diamination of conjugated dienes, see: Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308.
    • For a recent Pd(II)-catalyzed intermolecular diamination of conjugated dienes, see: Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308.
  • 22
    • 33846624362 scopus 로고    scopus 로고
    • For Pd(0)-catalyzed intermolecular diamination of conjugated dienes and trienes using di-tert-butyldiaziridinone, see: Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762.
    • For Pd(0)-catalyzed intermolecular diamination of conjugated dienes and trienes using di-tert-butyldiaziridinone, see: Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762.
  • 25
    • 34547198807 scopus 로고    scopus 로고
    • For Cu(I)-catalyzed intermolecular diamination of conjugated dienes and trienes using di-tert-butyldiaziridinone, see: Yuan, W.; Du, H.; Zhao, B.; Shi, Y. Org. Lett. 2007, 9, 2589.
    • For Cu(I)-catalyzed intermolecular diamination of conjugated dienes and trienes using di-tert-butyldiaziridinone, see: Yuan, W.; Du, H.; Zhao, B.; Shi, Y. Org. Lett. 2007, 9, 2589.
  • 27
    • 45549088414 scopus 로고    scopus 로고
    • For Cu(I)-catalyzed intermolecular diamination of conjugated dienes, trienes, and activated terminal olefins using diaziridinimine, see: Zhao, B.; Du, H.; Shi, Y. Org. Lett. 2008, 10, 1087.
    • For Cu(I)-catalyzed intermolecular diamination of conjugated dienes, trienes, and activated terminal olefins using diaziridinimine, see: Zhao, B.; Du, H.; Shi, Y. Org. Lett. 2008, 10, 1087.
  • 28
    • 34250863844 scopus 로고    scopus 로고
    • For Pd(0)-catalyzed intermolecular allylic and homoallylic C-H diamination of terminal olefins using di-tert-butyldiaziridinone, see: Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496.
    • For Pd(0)-catalyzed intermolecular allylic and homoallylic C-H diamination of terminal olefins using di-tert-butyldiaziridinone, see: Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496.
  • 30
    • 54249146835 scopus 로고    scopus 로고
    • For Pd(0)-catalyzed dehydrogenative diamination of terminal olefins using di-tert-butylthiadiaziridine 1,1-dioxide, see: Wang, B.; Du, H.; Shi, Y. Angew. Chem., Int. Ed. 2008, 47, 8224.
    • For Pd(0)-catalyzed dehydrogenative diamination of terminal olefins using di-tert-butylthiadiaziridine 1,1-dioxide, see: Wang, B.; Du, H.; Shi, Y. Angew. Chem., Int. Ed. 2008, 47, 8224.
  • 31
    • 36849045727 scopus 로고    scopus 로고
    • For Cu(I)-catalyzed intermolecular diamination of activated terminal olefins using di-tert-butylthiadiaziridine 1,1-dioxide, see: Zhao, B.; Yuan, W.; Du, H.; Shi, Y. Org. Lett. 2007, 9, 4943.
    • For Cu(I)-catalyzed intermolecular diamination of activated terminal olefins using di-tert-butylthiadiaziridine 1,1-dioxide, see: Zhao, B.; Yuan, W.; Du, H.; Shi, Y. Org. Lett. 2007, 9, 4943.
  • 33
    • 0003593740 scopus 로고
    • For a leading review on diaziridinones, see:, Hassner, A, Ed, John Wiley & Sons, Inc, Hoboken, NJ
    • For a leading review on diaziridinones, see: Heine, H. W. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 1983; p 547.
    • (1983) The Chemistry of Heterocyclic Compounds , pp. 547
    • Heine, H.W.1
  • 37
    • 0001186123 scopus 로고    scopus 로고
    • Timberlake, J. W.; Alender, J.; Garner, A. W.; Hodges, M. L.; Ö zmeral, C.; Szilagyi, S.; Jacobus, J. O. J. Org. Chem. 1981, 46, 2082.
    • Timberlake, J. W.; Alender, J.; Garner, A. W.; Hodges, M. L.; Ö zmeral, C.; Szilagyi, S.; Jacobus, J. O. J. Org. Chem. 1981, 46, 2082.
  • 41
    • 66149189235 scopus 로고    scopus 로고
    • When the CuCl-catalyzed diamination of 2-phenylpropene was carried out with di-tert-butylthiadiaziridine 1,1-dioxide or 1,2-di-tert- butyl-3-(cyanimino)diaziridine as the nitrogen source under the previously reported conditions (refs 9 and 12), only a small amount of diamination product or a messy mixtutre was obtained, respectively.
    • When the CuCl-catalyzed diamination of 2-phenylpropene was carried out with di-tert-butylthiadiaziridine 1,1-dioxide or 1,2-di-tert- butyl-3-(cyanimino)diaziridine as the nitrogen source under the previously reported conditions (refs 9 and 12), only a small amount of diamination product or a messy mixtutre was obtained, respectively.
  • 42
    • 66149190597 scopus 로고    scopus 로고
    • Representative diamination procedure (Table 1, entry 1): To a 1.5 mL vial equipped with a stir bar were added CuCl (0.002 g, 0.02 mmol), triphenylphosphine (0.0052 g, 0.02 mmol), and CDCl3 (0.3 mL). After the mixture was stirred at room temperature for 10 min, 2-phenylpropene (1a) (0.047 g, 0.4 mmol) was added. The reaction mixture was warmed to 65 C using an oil bath with stirring, and di-tert-butyldiaziridinone (2) (0.136 g, 0.8 mmol) was added by syringe pump over 8 h. The reaction mixture was stirred at this temperature for an additional 1 h and purified by flash chromatography (silica gel, hexane/ether ) 10/1) to give diamination product 3a as a white solid (0.105 g, 91%).
    • Representative diamination procedure (Table 1, entry 1): To a 1.5 mL vial equipped with a stir bar were added CuCl (0.002 g, 0.02 mmol), triphenylphosphine (0.0052 g, 0.02 mmol), and CDCl3 (0.3 mL). After the mixture was stirred at room temperature for 10 min, 2-phenylpropene (1a) (0.047 g, 0.4 mmol) was added. The reaction mixture was warmed to 65 C using an oil bath with stirring, and di-tert-butyldiaziridinone (2) (0.136 g, 0.8 mmol) was added by syringe pump over 8 h. The reaction mixture was stirred at this temperature for an additional 1 h and purified by flash chromatography (silica gel, hexane/ether ) 10/1) to give diamination product 3a as a white solid (0.105 g, 91%).
  • 44
    • 66149167229 scopus 로고    scopus 로고
    • Diamination of olefin 9 with CuCl-PPh3 (1:1) (10 mol %) in CDCl3 at 65 C for 10 h gave compound 10 in 30% yield and 11 in 33% yield. Diamination of 9 with CuCl-(R)-DTBM-SEGPHOS (2:1) (10 mol %)8 in CDCl3 at 65 C for 10 h gave compound 10 in 32% yield and 11 in 29% yield.
    • Diamination of olefin 9 with CuCl-PPh3 (1:1) (10 mol %) in CDCl3 at 65 C for 10 h gave compound 10 in 30% yield and 11 in 33% yield. Diamination of 9 with CuCl-(R)-DTBM-SEGPHOS (2:1) (10 mol %)8 in CDCl3 at 65 C for 10 h gave compound 10 in 32% yield and 11 in 29% yield.
  • 46
    • 0141843601 scopus 로고    scopus 로고
    • For recent leading references on other approaches to 4,4-disubstituted-2- imidazolidinones, see
    • For recent leading references on other approaches to 4,4-disubstituted-2- imidazolidinones, see: Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 11836
    • Trost, B.M.1    Fandrick, D.R.2
  • 51
    • 66149165794 scopus 로고    scopus 로고
    • Reference 6
    • Reference 6.
  • 52
    • 66149170004 scopus 로고    scopus 로고
    • Reference 4a
    • Reference 4a.
  • 56
    • 66149162993 scopus 로고    scopus 로고
    • Reference 4d
    • Reference 4d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.