Diastereoselective anomeric oxygen to carbon rearrangements of silyl enol ether derivatives of lactols

Synlett

Volumn , Issue 10, 1998, Pages 1093-1095

  Dixon, Darren J ^a   Ley, Steven V ^a   Tate, Edward W ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002348183     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1867     Document Type: Article

References (10)

1. Levy, D.; Tang, C. The Chemistry of C-Glycosides, Pergamon, 1995, and references cited therein.
2. See also Buffet, M. B.; Dixon, D. J.; Edwards, G. L.; Ley, S. V.; Tate, E. W. Synlett, 1997, 1055.
3. For some related examples see: i) Reetz, M. T.; Mallerstarke, H. Ann. Chem., 1983, 10, 1726;
4. ii) Toshima, K.; Miyamoto, N.; Matsuo, G.; Nakata, M.; Matsumura, S. J. Chem. Soc. Chem. Commun., 1996, 1379;
5. iii) Uenishi, J.; Sohma, A.; Yonemitsu, O. Chem. Lett., 1996, 595;
6. iv) Craig, D.; Tierney, J. P.; Williamson, C. Tetrahedron Lett., 1997, 38, 4153; and references cited therein.
7. Weinreb, S. M.; Nahm, S. Tetrahedron Lett., 1981, 22, 3815.
8. 3).
9. Re-exposure of a single diastereoisomer to identical rearrangement conditions shows no evidence of equilibration to the other diastereoisomer over an extended period, indicating that the rearrangement proceeds under kinetic control.
10. The minor side products observed in this reaction were tentatively assigned as the rearrangement products of the endo enol ether.