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Volumn 72, Issue 5, 2007, Pages 1814-1817

Diastereoselective synthesis of 4,5′-bis-proline compounds via reductive dimerization of N-acyloxyiminium ions

Author keywords

[No Author keywords available]

Indexed keywords

MANNICH REACTIONS; METAL-FREE CATALYSTS; N-ACYLOXYIMINIUM IONS; PROLINE DIMERS;

EID: 33847620667     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062406l     Document Type: Article
Times cited : (11)

References (24)
  • 1
    • 0003727958 scopus 로고    scopus 로고
    • For excellent reviews on peptidomimetic chemistry, see: a, Abell, A, Ed, JAI Press: Stamford, CT
    • For excellent reviews on peptidomimetic chemistry, see: (a) Advances in Amino Acid Mimetics and Peptidomimetics; Abell, A., Ed.; JAI Press: Stamford, CT, 1999: Vol. 2.
    • (1999) Advances in Amino Acid Mimetics and Peptidomimetics , vol.2
  • 2
    • 33847612125 scopus 로고    scopus 로고
    • Synthesis of Peptides and Peptidomimetics. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Georg Thieme Verlag: Stuttgart, 2003; E22c.
    • (b) Synthesis of Peptides and Peptidomimetics. In Houben-Weyl, Methods of Organic Chemistry, 4th ed.; Goodman, M., Felix, A., Moroder, L., Toniolo, C., Eds.; Georg Thieme Verlag: Stuttgart, 2003; Vol. E22c.
  • 5
    • 33750366006 scopus 로고    scopus 로고
    • Few examples of enamine-iminium ion dimerization reactions have been reported: (a) Kobayashi, S.; Gustafsson, T.; Shimizu, Y.: Kiyohara, H.; Matsubara, R. Org. Lett. 2006, 8, 4923-4925.
    • Few examples of enamine-iminium ion dimerization reactions have been reported: (a) Kobayashi, S.; Gustafsson, T.; Shimizu, Y.: Kiyohara, H.; Matsubara, R. Org. Lett. 2006, 8, 4923-4925.
  • 7
    • 33847678678 scopus 로고    scopus 로고
    • Kuehne, M. E.; Shannon, P. J. J. Org. Chem. 1977, 42, 2082-2087. See also: Maryanoff, B. E.; Zhang, H. C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431-1628.
    • (c) Kuehne, M. E.; Shannon, P. J. J. Org. Chem. 1977, 42, 2082-2087. See also: Maryanoff, B. E.; Zhang, H. C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431-1628.
  • 10
    • 33847655849 scopus 로고    scopus 로고
    • While various Lewis acids may be successfully employed to generate iminium ions in situ from N,O-acetals (e.g, TBSOTf, TMSOTf, BF 3-OEt2, the choice of the reducing agent (Sml2) proved to be critical, as shown in Table 1
    • 2), the choice of the reducing agent (Sml2) proved to be critical, as shown in Table 1.
  • 11
    • 33847660199 scopus 로고    scopus 로고
    • Unsatisfactory results were obtained when other solvents mixtures with coordinating additives were employed e.g, THF/HMPA, THF/ DMPU
    • Unsatisfactory results were obtained when other solvents mixtures with coordinating additives were employed (e.g., THF/HMPA, THF/ DMPU).
  • 12
    • 33847659772 scopus 로고    scopus 로고
    • Similarly, the stereostructures of minor isomers 9 and 10 were ascertained by 1D- and 2D-NMR analysis of the corresponding N,N-deprotected compounds. See the Supporting Information.
    • Similarly, the stereostructures of minor isomers 9 and 10 were ascertained by 1D- and 2D-NMR analysis of the corresponding N,N-deprotected compounds. See the Supporting Information.
  • 19
    • 4143094833 scopus 로고    scopus 로고
    • Houk, K. N., List, B., Eds. Acc. Chem. Res. 2004, 37, 487 (special issue on organocatalysis).
    • (b) Houk, K. N., List, B., Eds. Acc. Chem. Res. 2004, 37, 487 (special issue on organocatalysis).
  • 24
    • 33847657674 scopus 로고    scopus 로고
    • Lowering the catalyst loading to 10 mol, resulted in a prolonged reaction time and diminished enantioselectivity
    • Lowering the catalyst loading to 10 mol % resulted in a prolonged reaction time and diminished enantioselectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.