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Volumn 65, Issue 20, 2000, Pages 6423-6426

Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; AMINE; FERROCENYLMETHYL; GLYCINE DERIVATIVE; IRON DERIVATIVE; OXAZOLIDINE DERIVATIVE; PHENYLGLYCINOL; PROPARGYLAMINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034613353     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0003706     Document Type: Article
Times cited : (52)

References (33)
  • 5
    • 0033607471 scopus 로고    scopus 로고
    • and references herein cited
    • For recent examples of preparation of α-substituted propargylic amines in a racemic form, see: Mecozzi, T.; Petrini, M. J. Org. Chem. 1999, 64, 8970 and references herein cited. For preparation of α-substituted propargylic hydroxylamines, see: Franz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245.
    • (1999) J. Org. Chem. , vol.64 , pp. 8970
    • Mecozzi, T.1    Petrini, M.2
  • 6
    • 0033537047 scopus 로고    scopus 로고
    • For recent examples of preparation of α-substituted propargylic amines in a racemic form, see: Mecozzi, T.; Petrini, M. J. Org. Chem. 1999, 64, 8970 and references herein cited. For preparation of α-substituted propargylic hydroxylamines, see: Franz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 11245
    • Franz, D.E.1    Fässler, R.2    Carreira, E.M.3
  • 7
    • 0001300393 scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. (i) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1980) Angew. Chem. , pp. 753
    • Kolb, M.1    Barth, J.2
  • 8
    • 0025329413 scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. (i) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3957
    • Chung, J.Y.L.1    Wasicak, J.T.2
  • 9
    • 0026553743 scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. (i) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1992) J. Org. Chem. , vol.57 , pp. 2060
    • Manfré, F.1    Kern, J.-M.2    Biellmann, J.-F.3
  • 10
    • 84987589362 scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. (i) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1993) Helv. Chim. Acta , vol.76 , pp. 402
    • Enders, D.1    Schankat, J.2
  • 11
    • 84987260386 scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. (i) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1995) Helv. Chim. Acta. , vol.78 , pp. 970
    • Enders, D.1    Schankat, J.2
  • 12
    • 0029996546 scopus 로고    scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. (i) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1996) J. Org. Chem. , vol.61 , pp. 3238
    • Marshall, J.A.1    Wolf, M.A.2
  • 13
    • 0032540430 scopus 로고    scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. (i) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1998) J. Org. Chem. , vol.63 , pp. 2711
    • Poerwono, H.1    Higashiyama, K.2    Takahashi, H.3
  • 14
    • 0032171335 scopus 로고    scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. (i) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6561
    • Rae, A.1    Ker, J.2    Tabor, A.B.3    Castro, J.4    Parsons, S.5
  • 15
    • 0032552116 scopus 로고    scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1998) Tetrahedron , pp. 10227
    • Reginato, G.1    Mordini, A.2    Degl'innocenti, A.3    Manganiello, S.4    Capperucci, A.5    Poli, G.6
  • 16
    • 0002629743 scopus 로고    scopus 로고
    • For asymmetric synthesis of propargylic amines, see: (a) Kolb, M.; Barth, J. Angew. Chem. 1980, 753. (b) Chung, J. Y. L.; Wasicak, J. T. Tetrahedron Lett. 1990, 31, 3957. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060. (d) Enders, D.; Schankat, J. Helv. Chim. Acta 1993, 76, 402. (e) Enders, D.; Schankat, J. Helv. Chim. Acta. 1995, 78, 970. (f) Marshall, J. A.; Wolf, M. A.; J. Org. Chem. 1996, 61, 3238. (g) Poerwono, H.; Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (h) Rae, A.; Ker, J.; Tabor, A. B.; Castro, J.; Parsons, S. Tetrahedron Lett. 1998, 39, 6561. (i) Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Manganiello, S.; Capperucci, A.; Poli, G. Tetrahedron 1998, 10227. (j) Rae, A.; Castro, J.; Tabor, A. B. J. Chem. Soc., Perkin Trans. 1 1999, 1943.
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 1943
    • Rae, A.1    Castro, J.2    Tabor, A.B.3
  • 17
  • 30
    • 0342794138 scopus 로고    scopus 로고
    • note
    • The unstability of primary α-substituted propargylamines has already been noticed, see: ref 4j.


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