Equilibrium in Ring Expansion Reactions of the Bromo Epoxides

Synlett

Volumn 1997, Issue 7, 1997, Pages 793-794

  Hayashi, Nobuyuki ^a   Fujiwara, Kenshu ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000732375     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5782     Document Type: Article

References (12)

1. Hayashi, N.; Fujiwara, K.; Murai, A. Chem. Lett. 1996, 341-342.
2. Hayashi, N.; Fujiwara, K.; Murai, A. Tetrahedron Lett, 1996, 37, 6173-6176.
3. In the above reference (1), the regioselectivity of a similar substrate was endo/exo = 3.8:1.
4. 1H-NMR spectrum with that of 3 prepared alternatively [epoxidation and acid-catalized cyclization of (4E)-6-(tert-butyldiphenylsilyloxy)-4-hexen-1-ol] after acetylation, respectively. The diastereomer of 2 or 3 was not detected at all.
5. 1H-NMR.
6. For the skeletal rearrangements, see: a) Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933-2935. b) Nakata, T.; Nomura, S.; Matsukura, H. Tetrahedron Lett. 1996, 37, 213-216. c) Nakata, T.; Nomura, S.; Matsukura, H.; Morimoto, M. Tetrahedron Lett. 1996, 37, 217-220.
7. For the skeletal rearrangements, see: a) Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933-2935. b) Nakata, T.; Nomura, S.; Matsukura, H. Tetrahedron Lett. 1996, 37, 213-216. c) Nakata, T.; Nomura, S.; Matsukura, H.; Morimoto, M. Tetrahedron Lett. 1996, 37, 217-220.
8. For the skeletal rearrangements, see: a) Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933-2935. b) Nakata, T.; Nomura, S.; Matsukura, H. Tetrahedron Lett. 1996, 37, 213-216. c) Nakata, T.; Nomura, S.; Matsukura, H.; Morimoto, M. Tetrahedron Lett. 1996, 37, 217-220.
9. 1H-NMR spectra and the crude weight, the transfomation of 5 into 4 took place very cleanly without decomposition of 5.
10. The structure of 8 was confirmed by NMR analysis on 8 converted from 11, which was prepared by epoxidation and acid-catalyzed cyclization of (5E)-7-(tert-butyldiphenylsilyloxy)-5-hepten-1-ol.
11. The oxepane 9 was prepared from the known compound 15 (Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5335-5340) as illustrated in Scheme 8.
12. The structure of 13 was confirmed by formylation of 9.