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Volumn 10, Issue 21, 2008, Pages 4775-4778

Highly diastereoselective addition of lithio vinyl sulfoxides to N-sulfinimines: An entry to enantiopure s-sulfinyl-2-5-cis-dihydropyrroles

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Indexed keywords


EID: 60949086481     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801878f     Document Type: Article
Times cited : (31)

References (47)
  • 1
    • 41149174128 scopus 로고    scopus 로고
    • For recent reports on the syntheses of enantiopure pyrrolidines, see: a
    • For recent reports on the syntheses of enantiopure pyrrolidines, see: (a) Jackson, S. K.; Karadeolian, A.; Driega, A. B.; Kerr, M. A. J. Am. Chem. Soc. 2008, 130, 4196-4201;
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 4196-4201
    • Jackson, S.K.1    Karadeolian, A.2    Driega, A.B.3    Kerr, M.A.4
  • 4
    • 45849086958 scopus 로고    scopus 로고
    • For recent synthesis using the sulfinyl group as chiral auxiliary: d
    • For recent synthesis using the sulfinyl group as chiral auxiliary: (d) Davis, F. A.; Zhang, J.; Qiu, H.; Wu, Y. Org. Lett. 2008, 10, 1433-1436.
    • (2008) Org. Lett , vol.10 , pp. 1433-1436
    • Davis, F.A.1    Zhang, J.2    Qiu, H.3    Wu, Y.4
  • 17
    • 0037127529 scopus 로고    scopus 로고
    • N-Sulfmimines in Aza-MBH: (c) Aggarwal, V. K.; Martin Castro, A. M.; Mereu, A.; Adams, H. Tetrahedron Lett. 2002, 43, 1577-1581.
    • N-Sulfmimines in Aza-MBH: (c) Aggarwal, V. K.; Martin Castro, A. M.; Mereu, A.; Adams, H. Tetrahedron Lett. 2002, 43, 1577-1581.
  • 19
    • 33846928203 scopus 로고    scopus 로고
    • Tosyl imines in Aza-MBH: (a) Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2007, 48, 4119-4122.
    • Tosyl imines in Aza-MBH: (a) Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2007, 48, 4119-4122.
  • 20
  • 28
    • 33751559719 scopus 로고    scopus 로고
    • For some recent applications of N-sulfinimines: (a) Davis, F. A. J. Org. Chem. 2006, 71, 8993-9003.
    • For some recent applications of N-sulfinimines: (a) Davis, F. A. J. Org. Chem. 2006, 71, 8993-9003.
  • 34
    • 0000948886 scopus 로고    scopus 로고
    • Precedents of diastereoselective reactions of imines and α-sulfinyl carbanions: (a) García Ruano, J. L.; Alcudia, A.; del Prado, M.; Barros, D.; Maestro, M. C.; Fernández, I. J. Org. Chem. 2000, 65, 2856-2862.
    • Precedents of diastereoselective reactions of imines and α-sulfinyl carbanions: (a) García Ruano, J. L.; Alcudia, A.; del Prado, M.; Barros, D.; Maestro, M. C.; Fernández, I. J. Org. Chem. 2000, 65, 2856-2862.
  • 38
    • 0027527467 scopus 로고    scopus 로고
    • Vinyl and dienyl suif oxides 2 are available in one step by the procedure of Craig: Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1993, 49, 11263-11304.
    • Vinyl and dienyl suif oxides 2 are available in one step by the procedure of Craig: Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1993, 49, 11263-11304.
  • 40
    • 0038106171 scopus 로고    scopus 로고
    • (b) Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
    • (1998) Chem. Rev , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 44
    • 4444303072 scopus 로고    scopus 로고
    • Previous epoxidation-cyclization procedures with analogous nitrogenated structures: (a) Wipf, P.; Stephenson, C. R. J.; Walczak, M. A. A. Org. Lett. 2004, 6, 3009-3012.
    • Previous epoxidation-cyclization procedures with analogous nitrogenated structures: (a) Wipf, P.; Stephenson, C. R. J.; Walczak, M. A. A. Org. Lett. 2004, 6, 3009-3012.
  • 46
    • 0141431971 scopus 로고    scopus 로고
    • In related epoxidation experiments with other reagents, we have observed that isolated mixtures of epoxides cyclized to mixtures of cis-and trans-hydroxymethyl pyrrolines in identical ratio to the oxiranes. Some examples of epoxidation of dienyl sulfoxides: (a) Fernández de la Pradilla, R.; Manzano, P.; Montera, C.; Priego, J.; Martínez-Ripoll, M.; Martínez-Cruz, L. A. J. Org. Chem. 2003, 68, 7755-7767.
    • In related epoxidation experiments with other reagents, we have observed that isolated mixtures of epoxides cyclized to mixtures of cis-and trans-hydroxymethyl pyrrolines in identical ratio to the oxiranes. Some examples of epoxidation of dienyl sulfoxides: (a) Fernández de la Pradilla, R.; Manzano, P.; Montera, C.; Priego, J.; Martínez-Ripoll, M.; Martínez-Cruz, L. A. J. Org. Chem. 2003, 68, 7755-7767.


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