Three-carbon ring-enlargement of ethereal oxonium ylides - A viable synthesis of medium-sized cyclic ketoethers

Chemical Communications

Volumn , Issue 9, 1996, Pages 1077-1078

  Oku, Akira ^a   Ohki, Shigeji ^a   Yoshida, Tomohiro ^a   Kimura, Kenji ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002900280     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001077     Document Type: Article

References (12)

1. K. Friedrich, U. Jansen and W. Kirmse, Tetrahedron Lett., 1985, 26, 193; L. Thijs and B. Zwannenburg, Tetrahedron, 1980, 36, 2145.
2. K. Friedrich, U. Jansen and W. Kirmse, Tetrahedron Lett., 1985, 26, 193; L. Thijs and B. Zwannenburg, Tetrahedron, 1980, 36, 2145.
3. I. Naito, A. Oku, N. Otani, Y. Fujiwara and Y. Tanimoto, J. Chem. Soc., Perkin Trans. 2, 1996, 725.
4. A. Padwa and S. F. Hornbuckle, Chem. Rev., 1991, 91, 281 and references cited therein.
5. A. Oku, K. Kimura and S. Ohwaki, Acta Chem. Scand. 1993, 47, 391.
6. J. S. Clark, S. A. Krowiak and L. J. Street, Tetrahedron Lett., 1993, 34, 4385; for carbonyl ylide: A. Padwa, Acc. Chem. Res., 1991, 24, 22; for ammonium ylide: F. G. West and B. N. Naidu, J. Am. Chem. Soc., 1994, 116, 8420 and references cited therein.
7. J. S. Clark, S. A. Krowiak and L. J. Street, Tetrahedron Lett., 1993, 34, 4385; for carbonyl ylide: A. Padwa, Acc. Chem. Res., 1991, 24, 22; for ammonium ylide: F. G. West and B. N. Naidu, J. Am. Chem. Soc., 1994, 116, 8420 and references cited therein.
8. J. S. Clark, S. A. Krowiak and L. J. Street, Tetrahedron Lett., 1993, 34, 4385; for carbonyl ylide: A. Padwa, Acc. Chem. Res., 1991, 24, 22; for ammonium ylide: F. G. West and B. N. Naidu, J. Am. Chem. Soc., 1994, 116, 8420 and references cited therein.
9. J. S. Clark and A. B. Holmes, Tetrahedron Lett., 1988, 29, 4333; M. J. Davis and C. J. Moody, Synlett., 1990, 93.
10. J. S. Clark and A. B. Holmes, Tetrahedron Lett., 1988, 29, 4333; M. J. Davis and C. J. Moody, Synlett., 1990, 93.
11. Diazoketones 1a,b were prepared from the corresponding THF- and THP-carbinols, 1c,d from lactones: T. Mukaiyama, K. Homma and H. Takenoshita, Chem. Lett., 1988, 1725.
12. Bicyclo[3.3.0]oxonium ion, an analogous species to 5 (m = n = 1), was independently generated from 2-(3′-bromopropyl)tetrahydrofuran to give exclusively an eight-membered cyclic ether, whereas 4′-bromobutyl derivative gave a ring-switched product, see T. Kamada, Ge-Oing, M. Abe and A. Oku, J. Chem. Soc., Perkin Trans. 1, 1996, 413.