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Volumn 4, Issue 8, 2002, Pages 1271-1274

Formation of Bicyclic Ethers from Lewis Acid Promoted Cyclizations of Cyclic Oxonium Ions

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ARTICLE;

EID: 0346195421     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025570d     Document Type: Article
Times cited : (32)

References (38)
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    • For the [3 + 5] annulation route to bicyclic ethers, see: Molander, G. A.; Eastwood, P. R. J. Org. Chem. 1995, 60, 4559-4565.
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    • Diastereomeric ratios: 3a, 1.4:1; 3b, 2.2:1; 3c, 2.3:1; 3d, 4.7:1; 3aOEt, 1.4:1.
    • Diastereomeric ratios: 3a, 1.4:1; 3b, 2.2:1; 3c, 2.3:1; 3d, 4.7:1; 3aOEt, 1.4:1.
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    • For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem. 2001, 113, 4676-4701; 2001, 40, 4544-4568.
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    • For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem. 2001, 113, 4676-4701; 2001, 40, 4544-4568.
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    • For reviews, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem. 2001, 113, 4676-4701; 2001, 40, 4544-4568.
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  • 32
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    • note
    • Δ4,5-isomer -72.22 kJ/mol. For 20, calculations predict the 3,4-isomer to be more stable by 4.66 kJ/mol. In this case, the ene-type pathway might dominate.
  • 33
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    • note
    • 13C signals in the region between 80 and 90 ppm (2 RCHOR carbons). The minor isomer 17c shows the expected four peaks.
  • 38
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    • + force field). (a) Saunders, M.; Houk, K. N.; Wu, Y.-D.; Still, W. C.; Lipton, M.; Chang, G.; Guida, W. C. J. Am. Chem. Soc. 1990, 112, 1419-1427. (b) Kolossváry, I.; Guida, W. C. J. Comput. Chem. 1993, 14, 691-698.
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    • Kolossváry, I.1    Guida, W.C.2


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