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Volumn 61, Issue 15, 1996, Pages 5004-5012

Lithiated γ-tosyl-substituted benzylmethallylamine: New γ-amino methallyl sulfone anions in organic synthesis

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[No Author keywords available]

Indexed keywords


EID: 0000420517     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9602478     Document Type: Article
Times cited : (20)

References (40)
  • 8
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    • For preparation and applications of this intermediate to the synthesis of γ-functionalized methallyl sulfones, see: Nájera, C.; Sansano, J. M. Tetrahedron 1992, 48, 5179-5190.
    • (1992) Tetrahedron , vol.48 , pp. 5179-5190
    • Nájera, C.1    Sansano, J.M.2
  • 13
    • 0040890197 scopus 로고
    • For the corresponding unsubstituted allyl organolithium compounds derived from methallylamines see: (a) Fitt, J. J.; Gschwend, H. W. J. Org. Chem. 1981, 46, 3349-3352. (b) Barluenga, J.; Fañanás, F. J.; Foubelo, F.; Yus, M. J. Chem. Soc., Chem. Commun. 1988, 1135-1136. (c) Barluenga, J.; González, R.; Fañanás, F. J. Tetrahedron Lett. 1992, 33, 7573-7574. (d) Foubelo, F. Ph.D. Thesis, University of Oviedo, 1989.
    • (1981) J. Org. Chem. , vol.46 , pp. 3349-3352
    • Fitt, J.J.1    Gschwend, H.W.2
  • 14
    • 37049083491 scopus 로고
    • For the corresponding unsubstituted allyl organolithium compounds derived from methallylamines see: (a) Fitt, J. J.; Gschwend, H. W. J. Org. Chem. 1981, 46, 3349-3352. (b) Barluenga, J.; Fañanás, F. J.; Foubelo, F.; Yus, M. J. Chem. Soc., Chem. Commun. 1988, 1135-1136. (c) Barluenga, J.; González, R.; Fañanás, F. J. Tetrahedron Lett. 1992, 33, 7573-7574. (d) Foubelo, F. Ph.D. Thesis, University of Oviedo, 1989.
    • (1988) J. Chem. Soc., Chem. Commun. , pp. 1135-1136
    • Barluenga, J.1    Fañanás, F.J.2    Foubelo, F.3    Yus, M.4
  • 15
    • 0026497552 scopus 로고
    • For the corresponding unsubstituted allyl organolithium compounds derived from methallylamines see: (a) Fitt, J. J.; Gschwend, H. W. J. Org. Chem. 1981, 46, 3349-3352. (b) Barluenga, J.; Fañanás, F. J.; Foubelo, F.; Yus, M. J. Chem. Soc., Chem. Commun. 1988, 1135-1136. (c) Barluenga, J.; González, R.; Fañanás, F. J. Tetrahedron Lett. 1992, 33, 7573-7574. (d) Foubelo, F. Ph.D. Thesis, University of Oviedo, 1989.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7573-7574
    • Barluenga, J.1    González, R.2    Fañanás, F.J.3
  • 16
    • 0040890197 scopus 로고
    • Ph.D. Thesis, University of Oviedo
    • For the corresponding unsubstituted allyl organolithium compounds derived from methallylamines see: (a) Fitt, J. J.; Gschwend, H. W. J. Org. Chem. 1981, 46, 3349-3352. (b) Barluenga, J.; Fañanás, F. J.; Foubelo, F.; Yus, M. J. Chem. Soc., Chem. Commun. 1988, 1135-1136. (c) Barluenga, J.; González, R.; Fañanás, F. J. Tetrahedron Lett. 1992, 33, 7573-7574. (d) Foubelo, F. Ph.D. Thesis, University of Oviedo, 1989.
    • (1989)
    • Foubelo, F.1
  • 19
    • 3743122954 scopus 로고
    • For a recent review of saturated nitrogen heterocycles see: Steele, J. Contemp. Org. Synth. 1994, 95-112.
    • (1994) Contemp. Org. Synth. , pp. 95-112
    • Steele, J.1
  • 21
    • 3743081754 scopus 로고
    • a values of dimethylsulfone and diethylamine are 23 and 36, respectively: Eisch, J. J.; Galle, J. E. J. Org. Chem. 1980, 45, 4536-4538.
    • (1980) J. Org. Chem. , vol.45 , pp. 4536-4538
    • Eisch, J.J.1    Galle, J.E.2
  • 22
    • 3743070576 scopus 로고    scopus 로고
    • note
    • 6b with ethyl crotonate.
  • 23
    • 3743071648 scopus 로고    scopus 로고
    • note
    • Torsion angles for the most stable conformer were determined using Molecular Mechanics calculations: Hyperchem V3.0 from Hypercube, Inc., and Autodesk, Inc., using the MM+ force field. Coupling constants values were calculated using the program Altona developed by C. M. Cerdá-García-Rojas, L. Gerardo, and P. Joseph-Nathan.
  • 26
    • 3743092721 scopus 로고    scopus 로고
    • note
    • 5
  • 29
    • 3743063832 scopus 로고    scopus 로고
    • These compounds were very unstable and decomposed on standing
    • These compounds were very unstable and decomposed on standing.
  • 30
    • 0026721571 scopus 로고
    • For a recent review about eight-membered rings see: Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757-5821.
    • (1992) Tetrahedron , vol.48 , pp. 5757-5821
    • Petasis, N.A.1    Patane, M.A.2
  • 35
    • 3743079505 scopus 로고    scopus 로고
    • note
    • 2O content measured gas chromatographically) does not allow the determination of %D content. Thus, calculated %H/D values are corrected considering this fact.
  • 36
    • 3743103854 scopus 로고    scopus 로고
    • note
    • Diffractometer control program. For 20g: CAD4-PC, Delft Instruments X-ray Diffraction bv, Delft, The Netherlands, 1993. For 20i: CAD4-PC V 1.5c, Delft Instruments X-ray Diffraction bv, Delft, The Netherlands, 1994.
  • 37
    • 3743116193 scopus 로고    scopus 로고
    • note
    • 29 were done on a Hewlett-Packard 715/50 (HP-UX V9.01).
  • 40
    • 3743140725 scopus 로고    scopus 로고
    • note
    • The author has deposited atomic coordinates for 20g,i with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.