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Volumn 1, Issue 15, 2003, Pages 2699-2709

Solid-phase synthesis of 4-methylene pyrrolidines and allylic amines using palladium-activated allylic linkers

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSTS; PALLADIUM; PHENOLS; SYNTHESIS (CHEMICAL);

EID: 0141618488     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b303752e     Document Type: Article
Times cited : (16)

References (70)
  • 19
    • 0033574590 scopus 로고    scopus 로고
    • (c) I. W. James, Tetrahedron, 1999, 55, 4855-4946;
    • (1999) Tetrahedron , vol.55 , pp. 4855-4946
    • James, I.W.1
  • 28
    • 0032568384 scopus 로고    scopus 로고
    • (f) F. Guibé, Tetrahedron, 1998, 54, 2967-3042.
    • (1998) Tetrahedron , vol.54 , pp. 2967-3042
    • Guibé, F.1
  • 29
    • 0002177913 scopus 로고    scopus 로고
    • ed. I. Ojima, Wiley-VCH, New York, 2nd edn.
    • For reviews on allylic substitution see: (a) B. M. Trost and C. Lee, in Asymmetric Allylic Alkylation Reactions, ed. I. Ojima, Wiley-VCH, New York, 2nd edn., 2000, pp. 593-649; (b) P. Metz, in Houben-Weyl, Stereoselective Synthesis, E21e, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Georg Thieme Verlag, Stuttgart, 1995, pp. 5643-5669; (c) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; (d) J. A. Davies, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergammon Press, Oxford, UK, 1995; (e) S. Brase, J. H. Kirchhoff and J. Kobberling, Tetrahedron, 2003, 59, 885-939.
    • (2000) Asymmetric Allylic Alkylation Reactions , pp. 593-649
    • Trost, B.M.1    Lee, C.2
  • 30
    • 0141465460 scopus 로고
    • ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Georg Thieme Verlag, Stuttgart
    • For reviews on allylic substitution see: (a) B. M. Trost and C. Lee, in Asymmetric Allylic Alkylation Reactions, ed. I. Ojima, Wiley-VCH, New York, 2nd edn., 2000, pp. 593-649; (b) P. Metz, in Houben-Weyl, Stereoselective Synthesis, E21e, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Georg Thieme Verlag, Stuttgart, 1995, pp. 5643-5669; (c) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; (d) J. A. Davies, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergammon Press, Oxford, UK, 1995; (e) S. Brase, J. H. Kirchhoff and J. Kobberling, Tetrahedron, 2003, 59, 885-939.
    • (1995) Houben-Weyl, Stereoselective Synthesis, E21e , pp. 5643-5669
    • Metz, P.1
  • 31
    • 0003624033 scopus 로고
    • Academic Press, London
    • For reviews on allylic substitution see: (a) B. M. Trost and C. Lee, in Asymmetric Allylic Alkylation Reactions, ed. I. Ojima, Wiley-VCH, New York, 2nd edn., 2000, pp. 593-649; (b) P. Metz, in Houben-Weyl, Stereoselective Synthesis, E21e, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Georg Thieme Verlag, Stuttgart, 1995, pp. 5643-5669; (c) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; (d) J. A. Davies, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergammon Press, Oxford, UK, 1995; (e) S. Brase, J. H. Kirchhoff and J. Kobberling, Tetrahedron, 2003, 59, 885-939.
    • (1985) Palladium Reagents in Organic Synthesis
    • Heck, R.F.1
  • 32
    • 0003625966 scopus 로고
    • Ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergammon Press, Oxford, UK
    • For reviews on allylic substitution see: (a) B. M. Trost and C. Lee, in Asymmetric Allylic Alkylation Reactions, ed. I. Ojima, Wiley-VCH, New York, 2nd edn., 2000, pp. 593-649; (b) P. Metz, in Houben-Weyl, Stereoselective Synthesis, E21e, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Georg Thieme Verlag, Stuttgart, 1995, pp. 5643-5669; (c) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; (d) J. A. Davies, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergammon Press, Oxford, UK, 1995; (e) S. Brase, J. H. Kirchhoff and J. Kobberling, Tetrahedron, 2003, 59, 885-939.
    • (1995) Comprehensive Organometallic Chemistry II
    • Davies, J.A.1
  • 33
    • 0037429030 scopus 로고    scopus 로고
    • For reviews on allylic substitution see: (a) B. M. Trost and C. Lee, in Asymmetric Allylic Alkylation Reactions, ed. I. Ojima, Wiley-VCH, New York, 2nd edn., 2000, pp. 593-649; (b) P. Metz, in Houben-Weyl, Stereoselective Synthesis, E21e, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Georg Thieme Verlag, Stuttgart, 1995, pp. 5643-5669; (c) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; (d) J. A. Davies, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergammon Press, Oxford, UK, 1995; (e) S. Brase, J. H. Kirchhoff and J. Kobberling, Tetrahedron, 2003, 59, 885-939.
    • (2003) Tetrahedron , vol.59 , pp. 885-939
    • Brase, S.1    Kirchhoff, J.H.2    Kobberling, J.3
  • 34
  • 35
  • 36
    • 0001540138 scopus 로고    scopus 로고
    • For an example of an allylic sulfone linker see ref. 12
    • Two examples of "reversed" allylic linkers have been published by others. For an example of an allylic carboxylate see: S. C. Schürer and S. Blechert, Synlett, 1998, 166-168. For an example of an allylic sulfone linker see ref. 12.
    • (1998) Synlett , pp. 166-168
    • Schürer, S.C.1    Blechert, S.2
  • 39
    • 0000414496 scopus 로고
    • For a review of the Mitsunobu reaction see: D. L. Hughes, Org. Reactions, 1992, 42, 335-656.
    • (1992) Org. Reactions , vol.42 , pp. 335-656
    • Hughes, D.L.1
  • 48
    • 0034625424 scopus 로고    scopus 로고
    • For general references to N-acyliminium ion chemistry see: W. N. Speckamp and M. J. Moolenaar, Tetrahedron, 2000, 56, 3817-3856.
    • (2000) Tetrahedron , vol.56 , pp. 3817-3856
    • Speckamp, W.N.1    Moolenaar, M.J.2
  • 50
    • 0018322523 scopus 로고
    • The loading of the resins 20 and 36 were estimated using the Fmoc method after coupling with H-Lys(Fmoc)-OMe-HCl or Fmoc-AlaOH respectively. J. Meienhofer, M. Waki, E. P. Heimer, T. J. Lambros, R. C. Makofske and C. D. Chang, Int. J. Pept. Protein Res., 1979, 13, 35-42. Molar quantities and product yields are calculated on the basis that all the reaction steps on the solid-phase proceed in quantitative yield. Some variation in the estimated batch loadings of resins 20 and 36 was observed, and this is reflected in some of the yields when compared to our initial communication of this work.
    • (1979) Int. J. Pept. Protein Res. , vol.13 , pp. 35-42
    • Meienhofer, J.1    Waki, M.2    Heimer, E.P.3    Lambros, T.J.4    Makofske, R.C.5    Chang, C.D.6
  • 62
    • 0001640928 scopus 로고    scopus 로고
    • For the solid-phase synthesis of aryl ethers via the Mitsunobu reaction see: D. L. Hughes, Org. Prep. Proced. Int., 1996, 28, 127-164.
    • (1996) Org. Prep. Proced. Int. , vol.28 , pp. 127-164
    • Hughes, D.L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.