Huboux, Alexandre H., et al. “Preparation of Cyclohexenyl Derivatives by the Ring-Opening Reactions of Oxabicyclo[2.2.1] Compounds With Cuprates”. Tetrahedron Letters, vol. 31, no. 23, 1990, pp. 3253-6, https://doi.org/10.1016/S0040-4039(00)89036-X.

Genre

  • Journal Article
Contributors
Author: Huboux, Alexandre H.
Author: Lautens, Mark
Author: Smith, A. Catherine
Author: Abd-El-Aziz, Alaa S.
Date Issued
1990
Abstract

The ring-opening reaction of 7-oxabicyclo[2.2.1]hept-5-enes with cuprates is described. SN2′ attack with retention of configuration is the predominant pathway. The ring opening reaction of symmetrical and unsymmetrical 7-oxabicyclo[2.2.1]heptenes using cuprates is described. High yields of cyclohexenyl compounds such as 1 are isolated.

Note

Dep. Chem., Univ. Toronto, Toronto, ON, Can.

Source type: Electronic(1)

Language

  • English

Subjects

  • Ring cleavage (regioselective, of oxabicycloheptenes with organocuprates, cyclohexenols from)
  • prepn
  • ring
  • stereoselective
  • oxabicycloheptene
  • Stereochemistry (of ring cleavage of oxabicycloheptenes with organocuprates)
  • cyclohexenol
  • alkyl
  • cleavage
  • Ring cleavage (stereoselective, of oxabicycloheptenes with organocuprates, cyclohexenols from)
  • silyloxymethyl
  • Regiochemistry
  • regioselective
Page range
3253-3256
Host Title
Tetrahedron letters
Host Abbreviated Title
Tetrahedron Lett.
Volume
31
Issue
23
ISSN
0040-4039
DOI
https://doi.org/10.1016/S0040-4039(00)89036-X

Department