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Volumn 4, Issue 15, 2002, Pages 2537-2540

Stereoselective synthesis of trans β-lactams through iridium-catalyzed reductive coupling of imines and acrylates

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; BETA LACTAM; IMINE; IRIDIUM;

EID: 0041382872     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020106u     Document Type: Article
Times cited : (68)

References (33)
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    • (b) For lead references, see: Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Daniel, K. L. Tetrahedron Lett. 1992, 33, 7819. Anada, M.; Hashimoto, S.-I. Tetrahedron Lett. 1998, 39, 9063.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9063
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    • (c) Miura, M.; Enna, M.; Okura, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999. Lo, M. M-C.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572.
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  • 17
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    • For early reports on nonstereoselective reductive aldol reactions, see: (c) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809-4812.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4809-4812
    • Revis, A.1    Hilty, T.K.2
  • 21
    • 0000862669 scopus 로고    scopus 로고
    • For a review of catalytic enantioselective addition to imines, see: Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
    • (1999) Chem. Rev. , vol.99 , pp. 1069-1094
    • Kobayashi, S.1    Ishitani, H.2
  • 23
    • 84872277981 scopus 로고    scopus 로고
    • note
    • Fast Red TR salt (4-chloro-2-methylbenzenediazonium chloride) is commercially available from Aldrich Chemical Co.
  • 24
    • 0023149442 scopus 로고
    • The PMP group is readily removed from the β-lactam nitrogen under CAN oxidation conditions, see: (a) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 109, 1129-1135.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 1129-1135
    • Georg, G.I.1    Kant, J.2    Gill, H.S.3
  • 26
    • 0012627974 scopus 로고
    • Addition of an Ir(I) hydride to methyl acrylate in the presence of dioxygen is proposed to provide a C-bound iridium enolate. See: Droiun, M.; Harrod, J. F. Can. J. Chem. 1985, 63, 353-360.
    • (1985) Can. J. Chem. , vol.63 , pp. 353-360
    • Droiun, M.1    Harrod, J.F.2
  • 27
    • 0033575073 scopus 로고    scopus 로고
    • For addition of Pd enolates to imines, see: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450-5458. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5450-5458
    • Fujii, A.1    Hagiwara, E.2    Sodeoka, M.3
  • 28
    • 0032542749 scopus 로고    scopus 로고
    • For addition of Pd enolates to imines, see: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450-5458. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2474-2475
    • Hagiwara, E.1    Fujii, A.2    Sodeoka, M.3
  • 29
    • 0000356761 scopus 로고
    • Lithium enolates of aryl esters eliminate to ketene upon warming to room temperature. See: Seebach, D.; Amstutz, R.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1985, 107, 5403-5409. The reverse reaction with addition of a Pd-alkoxide to ketene is postulated in a review article. See: Geoffroy, G. L.; Bassner, S. L. In Advances in Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: San Diego, 1993; Vol. 28, p 6.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 5403-5409
    • Seebach, D.1    Amstutz, R.2    Laube, T.3    Schweizer, W.B.4    Dunitz, J.D.5
  • 30
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    • Stone, F. G. A., West, R., Eds.; Academic Press: San Diego
    • Lithium enolates of aryl esters eliminate to ketene upon warming to room temperature. See: Seebach, D.; Amstutz, R.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1985, 107, 5403-5409. The reverse reaction with addition of a Pd-alkoxide to ketene is postulated in a review article. See: Geoffroy, G. L.; Bassner, S. L. In Advances in Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: San Diego, 1993; Vol. 28, p 6.
    • (1993) Advances in Organometallic Chemistry , vol.28 , pp. 6
    • Geoffroy, G.L.1    Bassner, S.L.2
  • 31
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    • [2 + 2] cycloaddition of imine 1 and methyl ketene is reported to give only the trans stereoisomer when the ketene is generated from pyrolysis of 2-butanone. See: Tschamber, T.; Streith, J. Tetrahedron Lett. 1980, 21, 4503-4506.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 4503-4506
    • Tschamber, T.1    Streith, J.2
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    • note
    • [2 + 2] ketene-imine cycloaddition is proposed to proceed through a zwiterionic iminium ion generated by nucleophilic addition of the imine to ketene. For a review, see: ref 1b, pp 295-368.


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