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Volumn 69, Issue 1, 2004, Pages 122-129

A Versatile Stereoselective Synthesis of endo,exo-Furofuranones: Application to the Enantioselective Synthesis of Furofuran Lignans

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL BONDS; DERIVATIVES; OXIDATION; REACTION KINETICS; RHODIUM; SYNTHESIS (CHEMICAL);

EID: 0346731102     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035365r     Document Type: Article
Times cited : (65)

References (79)
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    • Ghosez has reported auxiliary-based methods for the asymmetric [242] keteniminium-olefin cycloaddition. However, in the reactions of enantiomerically enriched keteniminium salts with terminal olefins, enantioselectivities were moderate (0-76% ee): (a) Houge, C.; Frisque-Hesbain, A. M.; Mockel, A.; Ghosez, L.; Declercq, J. P.; Germain, G.; Van Meerssche, M. J. Am. Chem. Soc. 1982, 104, 2920.
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  • 44
    • 0030912922 scopus 로고    scopus 로고
    • Copper-catalyzed intramolecular cyclopropanation of the diazoderivative of 11 was also investigated, providing 12 in 42% yield as a 7:3 mixture of diastereoisomers. No further efforts were made to improve this alternative approach. For related cyclizations: Molander, G. A.; Alonso-Alija, C. Tetrahedron 1997, 53, 8067.
    • (1997) Tetrahedron , vol.53 , pp. 8067
    • Molander, G.A.1    Alonso-Alija, C.2
  • 45
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    • Structures 27, 28, 35, 38b, and 1 were unambiguously determined by X-ray crystallography. It was also possible to confirm the absolute stereochemistry of 38b due to the presence of a heavy atom in the structure. Crystallographic data for these structures have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC 219596 (28), CCDC 219598 (35), CCDC 218116 (38b), and CCDC 219597 (1). The X-ray structure of 27 has been reported previously: Gelbrich, T.; Hursthouse, M. B. Acta Crystallogr. 2001, E57, o566.
    • (2001) Acta Crystallogr. , vol.E57
    • Gelbrich, T.1    Hursthouse, M.B.2
  • 47
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    • note
    • Personal Chemistry is thanked for the donation of the Smith-Synthesizer used in this work.
  • 48
    • 0003573091 scopus 로고
    • Van Nostrand Reinhold Company: New York
    • Although we have not experienced any problem in the handling or heating of these metal perchlorates, care should be taken when manipulating them due to their potentially explosive nature. Sax, N. I. Dangerous Properties of Industrial Materials, 5th ed.; Van Nostrand Reinhold Company: New York, 1979.
    • (1979) Dangerous Properties of Industrial Materials, 5th Ed.
    • Sax, N.I.1
  • 53
    • 0000864763 scopus 로고
    • 3 and used in diazotransfer reactions without further purification: Reagan, M. T.; Nickon, A. J. Am. Chem. Soc. 1968, 90, 4096.
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    • Reagan, M.T.1    Nickon, A.2
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    • For reviews of metal-catalyzed C-H insertion of diazocompounds: (a) Doyle, M. P. Chem. Rev. 1986, 86, 919.
    • (1986) Chem. Rev. , vol.86 , pp. 919
    • Doyle, M.P.1
  • 60
    • 0001331380 scopus 로고
    • Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag
    • (b) Taber, D. F. In Houben Weyl, Methods of Stereoselective Synthesis, 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E21a, pp 1127-1148.
    • (1995) Houben Weyl, Methods of Stereoselective Synthesis, 4th Ed. , vol.E21A , pp. 1127-1148
    • Taber, D.F.1
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    • note
    • R (R)-alcohol = 29.2 ruin.
  • 71
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    • (b) Fang, J. M.; Lee, C. K.; Cheng, Y. S. Phytochemistry 1992, 31, 3659. Note that in ref 28b the structure of the wrong enantiomer is depicted. The structure of the synthetic sample of 1 prepared in our laboratory was unambiguously confirmed by X-ray crystallography (ref 16).
    • (1992) Phytochemistry , vol.31 , pp. 3659
    • Fang, J.M.1    Lee, C.K.2    Cheng, Y.S.3
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    • Synthesis of (±)-epipinoresinol: (b) Katayama, T.; Davin, L. B.; Chu, A.; Lewis, N. G. Phytochemistry 1993, 33, 581-591. (+)-Epipinoresinol from acid-catalyzed isomerization of (+)-pinoresinol: Nishibe, S.; Tsukamoto, H.; Hisada, S. Chem. Pharm. Bull. 1984, 32, 4653.
    • (1993) Phytochemistry , vol.33 , pp. 581-591
    • Katayama, T.1    Davin, L.B.2    Chu, A.3    Lewis, N.G.4
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    • Synthesis of (±)-epipinoresinol: (b) Katayama, T.; Davin, L. B.; Chu, A.; Lewis, N. G. Phytochemistry 1993, 33, 581-591. (+)-Epipinoresinol from acid-catalyzed isomerization of (+)-pinoresinol: Nishibe, S.; Tsukamoto, H.; Hisada, S. Chem. Pharm. Bull. 1984, 32, 4653.
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 4653
    • Nishibe, S.1    Tsukamoto, H.2    Hisada, S.3


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