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Volumn 65, Issue 7, 2000, Pages 1899-1906

Three- to six-carbon ring-enlargement reaction of cyclic ortho esters bearing a diazocarbonyl side chain. Use of the intramolecular formation of tricyclooxonium ylides

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; ESTER DERIVATIVE; OXONIC ACID;

EID: 0034616088     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991332t     Document Type: Article
Times cited : (23)

References (55)
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    • Baird, M.S.1    Baxter, A.G.W.2    Hoorter, A.3    Jefferion, I.4
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    • For intramolecular oxonium ylide formation, see: (a) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060. (b) Clark, J. S.; Dossetter, A. G.; Whittingham, W. G. Tetrahedron Lett. 1996, 37, 5603. (c) Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381. (d) ref 23. (e) Brogan, J. B.; Bauer, C. B.; Rogers, R. D.; Zercher, C. K. Tetrahedron Lett. 1996, 37, 5053.
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    • 0343657900 scopus 로고    scopus 로고
    • For intramolecular oxonium ylide formation, see: (a) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060. (b) Clark, J. S.; Dossetter, A. G.; Whittingham, W. G. Tetrahedron Lett. 1996, 37, 5603. (c) Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381. (d) ref 23. (e) Brogan, J. B.; Bauer, C. B.; Rogers, R. D.; Zercher, C. K. Tetrahedron Lett. 1996, 37, 5053.
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    • For intramolecular oxonium ylide formation, see: (a) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060. (b) Clark, J. S.; Dossetter, A. G.; Whittingham, W. G. Tetrahedron Lett. 1996, 37, 5603. (c) Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381. (d) ref 23. (e) Brogan, J. B.; Bauer, C. B.; Rogers, R. D.; Zercher, C. K. Tetrahedron Lett. 1996, 37, 5053.
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    • ref 23
    • For intramolecular oxonium ylide formation, see: (a) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060. (b) Clark, J. S.; Dossetter, A. G.; Whittingham, W. G. Tetrahedron Lett. 1996, 37, 5603. (c) Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381. (d) ref 23. (e) Brogan, J. B.; Bauer, C. B.; Rogers, R. D.; Zercher, C. K. Tetrahedron Lett. 1996, 37, 5053.
  • 18
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    • For intramolecular oxonium ylide formation, see: (a) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060. (b) Clark, J. S.; Dossetter, A. G.; Whittingham, W. G. Tetrahedron Lett. 1996, 37, 5603. (c) Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381. (d) ref 23. (e) Brogan, J. B.; Bauer, C. B.; Rogers, R. D.; Zercher, C. K. Tetrahedron Lett. 1996, 37, 5053.
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    • Reviews: (a) Reference 1a
    • Reviews: (a) Reference 1a. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
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    • note
    • This is not always the requisite because free carbenes such as alkylidenecarbenes bearing a cyclic acetal ring also undergo a similar enlargement. See ref 13.
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    • (b) Unpublished results: The deuterium scrambling reaction of dithiolane-substituted diazocarbonyl compounds indicated that both intra- and intermolecular proton-transfer reactions can take place with bicyclic sulfonium ylides.
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    • When AcOH was used in place of MeOH, the reaction resulted in the formation of a complex mixture.
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    • Other methods for preparing medium ring lactones by C-O bond formation: (a) Clark, J. S.; Holmes, A. B. Tetrahedron Lett. 1988, 34, 4333. (b) Asaoka, M.; Naito, S.; Takei, H. Tetrahedron Lett. 1985, 26, 2103. (c) Asaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715. (d) Boger, D. L.; Sakya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204.
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    • Other methods for preparing medium ring lactones by C-O bond formation: (a) Clark, J. S.; Holmes, A. B. Tetrahedron Lett. 1988, 34, 4333. (b) Asaoka, M.; Naito, S.; Takei, H. Tetrahedron Lett. 1985, 26, 2103. (c) Asaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715. (d) Boger, D. L.; Sakya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204.
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    • Other methods for preparing medium ring lactones by C-O bond formation: (a) Clark, J. S.; Holmes, A. B. Tetrahedron Lett. 1988, 34, 4333. (b) Asaoka, M.; Naito, S.; Takei, H. Tetrahedron Lett. 1985, 26, 2103. (c) Asaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715. (d) Boger, D. L.; Sakya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204.
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    • Other methods for preparing medium ring lactones by C-O bond formation: (a) Clark, J. S.; Holmes, A. B. Tetrahedron Lett. 1988, 34, 4333. (b) Asaoka, M.; Naito, S.; Takei, H. Tetrahedron Lett. 1985, 26, 2103. (c) Asaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715. (d) Boger, D. L.; Sakya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204.
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