메뉴 건너뛰기




Volumn 9, Issue 14, 2007, Pages 2633-2636

New insights into NIS-promoted aminocyclization. Synthesis of decahydroquinolines from 2-allylcyclohexylamines

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CYCLOHEXYLAMINE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; NICKEL; NICKEL SULFIDE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34547434793     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070770g     Document Type: Article
Times cited : (18)

References (47)
  • 3
    • 0000484771 scopus 로고    scopus 로고
    • Using iodine; (a) Tanner, D, Sellén, M, Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374-3378
    • Using iodine; (a) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374-3378.
  • 6
    • 34547396187 scopus 로고    scopus 로고
    • Using NIS: (a) Blough, B. E, Mascarella, S. W, Rothman, R. B, Carroll, F. I. J. Chem. Soc, Chem. Commun. 1993, 758-760
    • Using NIS: (a) Blough, B. E.; Mascarella, S. W.; Rothman, R. B.; Carroll, F. I. J. Chem. Soc., Chem. Commun. 1993, 758-760.
  • 12
    • 33746894523 scopus 로고    scopus 로고
    • For the t-BuOI-promoted cyclization of N-alkenylamides: Minakata, S.; Morino, Y.; Oderaoroshi, Y.; Komatsu, M. Org. Lett. 2006, 8, 3335-3337.
    • (d) For the t-BuOI-promoted cyclization of N-alkenylamides: Minakata, S.; Morino, Y.; Oderaoroshi, Y.; Komatsu, M. Org. Lett. 2006, 8, 3335-3337.
  • 30
    • 29144468045 scopus 로고    scopus 로고
    • Of the cyclohexylamines 3a-c and 4a-c here described, only 3a has been previously reported. This amine has been prepared by an enantioselective reduction of imine 2a: Ros, A.; Magriz, A.; Dietrich, H.; Ford, M.; Fernández, R.; Lassaletta, J. M. Adv. Synth. Catal. 2005, 347, 1917-1920.
    • Of the cyclohexylamines 3a-c and 4a-c here described, only 3a has been previously reported. This amine has been prepared by an enantioselective reduction of imine 2a: Ros, A.; Magriz, A.; Dietrich, H.; Ford, M.; Fernández, R.; Lassaletta, J. M. Adv. Synth. Catal. 2005, 347, 1917-1920.
  • 31
    • 27144470285 scopus 로고    scopus 로고
    • For a recent example of diastereoselective reduction of 2-substituted iminocyclohexanes, see
    • For a recent example of diastereoselective reduction of 2-substituted iminocyclohexanes, see: Sanderson, J. M.; Findlay, J. B. C.; Fishwick, C. W. G. Tetrahedron 2005, 61, 11244-11252.
    • (2005) Tetrahedron , vol.61 , pp. 11244-11252
    • Sanderson, J.M.1    Findlay, J.B.C.2    Fishwick, C.W.G.3
  • 34
    • 4544316937 scopus 로고    scopus 로고
    • 10 For another procedure to achieve 3-alkyl-2-allylcyclohexylamines, starting from 2-cyclohexenone, see
    • ( 10) For another procedure to achieve 3-alkyl-2-allylcyclohexylamines, starting from 2-cyclohexenone, see: Dijk, E. W.; Panella, L.; Pinho, P.; Naasz, R.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2004, 60, 9687-9693.
    • (2004) Tetrahedron , vol.60 , pp. 9687-9693
    • Dijk, E.W.1    Panella, L.2    Pinho, P.3    Naasz, R.4    Meetsma, A.5    Minnaard, A.J.6    Feringa, B.L.7
  • 35
    • 0032811082 scopus 로고    scopus 로고
    • For nucleophilic ring opening of bicyclic aziridinium ions, see: a
    • For nucleophilic ring opening of bicyclic aziridinium ions, see: (a) Cossy, J.; Dumas, C.; Pardo, D. G. Eur. J. Org. Chem. 1999, 1693-1699.
    • (1999) Eur. J. Org. Chem , pp. 1693-1699
    • Cossy, J.1    Dumas, C.2    Pardo, D.G.3
  • 39
    • 33847090061 scopus 로고    scopus 로고
    • For a classical conformational and configurational study on cis-decahydroquinolines: Vierhapper, F. W.; Eliel, E. L. J. Org. Chem. 1977, 42, 51-62.
    • For a classical conformational and configurational study on cis-decahydroquinolines: Vierhapper, F. W.; Eliel, E. L. J. Org. Chem. 1977, 42, 51-62.
  • 40
    • 33746876014 scopus 로고    scopus 로고
    • For the application of this protocol to the synthesis of cis-decahydroquinolines, see: Mena, M.; Bonjoch, J.; Gomez Pardo, D.; Cossy, J. J. Org. Chem. 2006, 71, 5930-5935. Figure Presented
    • For the application of this protocol to the synthesis of cis-decahydroquinolines, see: Mena, M.; Bonjoch, J.; Gomez Pardo, D.; Cossy, J. J. Org. Chem. 2006, 71, 5930-5935. Figure Presented
  • 41
    • 17844396203 scopus 로고    scopus 로고
    • For a semiempirical MO approach to the mechanism of the NIS-mediated nucleophilic addition, see
    • For a semiempirical MO approach to the mechanism of the NIS-mediated nucleophilic addition, see: Mota, A. J.; Castellanos, E.; Alvarez de Cienfuegos, L.; Robles, R. Tetrahedron: Asymmetry 2005, 16, 1615-1629.
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 1615-1629
    • Mota, A.J.1    Castellanos, E.2    Alvarez de Cienfuegos, L.3    Robles, R.4
  • 43
    • 0026029281 scopus 로고    scopus 로고
    • Interestingly, the aminocyclization of 2-allyl-N-tosylcyclohexylamines promoted by MCPBA oxidation always gives octahydroindole derivatives irrespective of the cis or trans relationship of the bishomoallylic amine used: Nuhrich, A.; Moulines, J. Tetrahedron 1991, 47, 3075-3088.
    • Interestingly, the aminocyclization of 2-allyl-N-tosylcyclohexylamines promoted by MCPBA oxidation always gives octahydroindole derivatives irrespective of the cis or trans relationship of the bishomoallylic amine used: Nuhrich, A.; Moulines, J. Tetrahedron 1991, 47, 3075-3088.
  • 44
    • 34547398776 scopus 로고    scopus 로고
    • Unlike 6, compounds 5 are conformationally heterogeneous at rt and showed very broad signals in their NMR spectra. Sharp and interpretable spectra of 5b were obtained at -20 °C.
    • Unlike 6, compounds 5 are conformationally heterogeneous at rt and showed very broad signals in their NMR spectra. Sharp and interpretable spectra of 5b were obtained at -20 °C.
  • 45
    • 0042670084 scopus 로고    scopus 로고
    • The NIS-promoted oxacyclization of frans-2-allylcyclohexanol gives an epimeric mixture of 2-iodomethylperhydrobenzofurane derivatives: Tanikaga, R.; Matsumoto, Y.; Sakaguchi, M.; Koyama, Y.; Ono, K. Tetrahedron Lett. 2003, 44, 6781-6783.
    • The NIS-promoted oxacyclization of frans-2-allylcyclohexanol gives an epimeric mixture of 2-iodomethylperhydrobenzofurane derivatives: Tanikaga, R.; Matsumoto, Y.; Sakaguchi, M.; Koyama, Y.; Ono, K. Tetrahedron Lett. 2003, 44, 6781-6783.
  • 46
    • 33745698645 scopus 로고    scopus 로고
    • (a) Weinreb, S. M. Chem. Rev. 2006, 106, 2531-2549.
    • (2006) Chem. Rev , vol.106 , pp. 2531-2549
    • Weinreb, S.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.