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Volumn 62, Issue 19, 1997, Pages 6687-6689

Diastereoselective coupling reaction of activated cyclic ketene ortho ester with aldehydes promoted by Lewis acid catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ESTER DERIVATIVE; KETENE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; TIN CHLORIDE;

EID: 0030765373     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9707747     Document Type: Article
Times cited : (8)

References (18)
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  • 2
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    • CRC: New York
    • For general discussions, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Ager, D. J.; East, M. B. Asymmetric Synthetic Methodology; CRC: New York, 1996.
    • (1996) Asymmetric Synthetic Methodology
    • Ager, D.J.1    East, M.B.2
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    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • For reviews, see: (a) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 133. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 239. (c) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 301. (d) Heathcock, C. H. In Modern Synthetic Methods; Scheffold, R., Ed.; VCH: Basel, Swiss, 1992; p 1.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 133
    • Heathcock, C.H.1
  • 5
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    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • For reviews, see: (a) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 133. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 239. (c) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 301. (d) Heathcock, C. H. In Modern Synthetic Methods; Scheffold, R., Ed.; VCH: Basel, Swiss, 1992; p 1.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 239
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    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • For reviews, see: (a) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 133. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 239. (c) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 301. (d) Heathcock, C. H. In Modern Synthetic Methods; Scheffold, R., Ed.; VCH: Basel, Swiss, 1992; p 1.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 301
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    • For reviews, see: (a) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 133. (b) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 239. (c) Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, p 301. (d) Heathcock, C. H. In Modern Synthetic Methods; Scheffold, R., Ed.; VCH: Basel, Swiss, 1992; p 1.
    • (1992) Modern Synthetic Methods , pp. 1
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    • (1994) Organometallics in Synthesis , pp. 1
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  • 12
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    • note
    • 2 required the use of stoichiometric amounts of Lewis acid, presumably due to complexation of Lewis acid with product, and gave only yields in the range of 50%.
  • 13
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    • note
    • We tried to isolate intermediate 15 under various neutral or basic conditions, but unsuccessfully. The major component was always 9 along with several minor components. However, after mild acidic workup, 9 was cleanly obtainable.
  • 14
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    • Alliger, N. L., Eliel, E. L., Wilson, S. H., Eds.; Wiley: New York
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    • (1982) Topics in Stereochemistry , vol.13 , pp. 1
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    • Oxocarbenium intermediates in organic synthesis, see: (a) Molander, G. A.; Eastwood, P. R. J. Org. Chem. 1996, 61, 1910. (b) Petasis, N. A.; Lu, S.-P. J. Am. Chem. Soc. 1995, 117, 6394. (c) Paquette, L. A.; Branan, B. M.; Friedrich, D.; Edmondson, S. D.; Rogers, R. D. J. Am. Chem. Soc. 1994, 116, 506.
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    • Molander, G.A.1    Eastwood, P.R.2
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    • Oxocarbenium intermediates in organic synthesis, see: (a) Molander, G. A.; Eastwood, P. R. J. Org. Chem. 1996, 61, 1910. (b) Petasis, N. A.; Lu, S.-P. J. Am. Chem. Soc. 1995, 117, 6394. (c) Paquette, L. A.; Branan, B. M.; Friedrich, D.; Edmondson, S. D.; Rogers, R. D. J. Am. Chem. Soc. 1994, 116, 506.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6394
    • Petasis, N.A.1    Lu, S.-P.2
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    • Oxocarbenium intermediates in organic synthesis, see: (a) Molander, G. A.; Eastwood, P. R. J. Org. Chem. 1996, 61, 1910. (b) Petasis, N. A.; Lu, S.-P. J. Am. Chem. Soc. 1995, 117, 6394. (c) Paquette, L. A.; Branan, B. M.; Friedrich, D.; Edmondson, S. D.; Rogers, R. D. J. Am. Chem. Soc. 1994, 116, 506.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 506
    • Paquette, L.A.1    Branan, B.M.2    Friedrich, D.3    Edmondson, S.D.4    Rogers, R.D.5


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