A HIGHLY Z-SELECTIVE ISOMERIZATION (DOUBLE-BOND MIGRATION) PROCEDURE FOR ALLYL ACETALS AND ALLYL ETHERS MEDIATED BY NICKEL-COMPLEXES

Authors
WILLE A TOMM S FRAUENRATH H
Citation
A. Wille et al., A HIGHLY Z-SELECTIVE ISOMERIZATION (DOUBLE-BOND MIGRATION) PROCEDURE FOR ALLYL ACETALS AND ALLYL ETHERS MEDIATED BY NICKEL-COMPLEXES, Synthesis, (3), 1998, pp. 305-308
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
3
Year of publication
1998
Pages
305 - 308
Database
ISI
SICI code
0039-7881(1998):3<305:AHZI(M>2.0.ZU;2-R
Abstract
A novel procedure for a highly Z-selective isomerization (double-bond migration) of acyclic allyl acetals and allyl ethers based on NiCl(2)d ppb catalysis by activation with Super-Hydride (lithium triethylborohy dride) is described. The stereochemical outcome is compared with the r esults obtained with Ru and Rh catalysts. The applicability of the new process is demonstrated in the stereoselective synthesis of Claisen s ubstrates (allyl vinyl ethers) from diallyl ethers.