Elsevier

Tetrahedron Letters

Volume 41, Issue 19, 6 May 2000, Pages 3731-3733
Tetrahedron Letters

RuO4-catalysed oxidative cyclisation of 1,6-dienes to trans-2,6-bis(hydroxymethyl)tetrahydropyranyldiols. A novel stereoselective process

https://doi.org/10.1016/S0040-4039(00)00476-7Get rights and content

Abstract

RuO4 catalyses the stereoselective oxidative cyclisation of the 1,6-dienes, 7-methyl-1,6-octadiene and 1,6-heptadiene, to the corresponding trans-2,6-bis(hydroxymethyl)tetrahydropyranyldiols, in the presence of NaIO4 as primary oxidant, in EtOAc:CH3CN:H2O (3:3:1) at 0°C for 4 min. A mechanistic hypothesis explaining the observed trans-2,6-stereochemical control is formulated.

Section snippets

Acknowledgements

We are grateful to MURST, Italy (PRIN 1997), for a grant in support of this investigation and to the ‘Centro di Metodologie Chimico-Fisiche dell'Università di Napoli ‘Federico II’ ’ for NMR facilities.

References (12)

  • Zeng, L.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. Nat. Prod. Rep. 1996,...
  • Tang, S.; Kennedy, R. M. Tetrahedron Lett. 1992, 33,...
  • McDonald, F. E.; Towne, T. B. J. Org. Chem. 1995, 60,...
  • (a) Klein, E.; Rojahn, W. Tetrahedron 1965, 21, 2353–2358. (b) Walba, D. M.; Wand, M. D.; Wilkes, M. C. J. Am. Chem....
  • Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46,...
  • de Champdoré, M.; Lasalvia, M.; Piccialli, V. Tetrahedron Lett. 1998, 39,...
There are more references available in the full text version of this article.

Cited by (38)

View all citing articles on Scopus
View full text