TITLE

Sequential olefin metathesis – Intramolecular asymmetric Heck reactions in the synthesis of polycycles

AUTHOR(S)
Lautens, Mark; Zunic, Valentin
PUB. DATE
February 2004
SOURCE
Canadian Journal of Chemistry;Feb2004, Vol. 82 Issue 2, p399
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
Application of the intramolecular asymmetric Heck reaction in the desymmetrization of a novel class of symmetrical bicyclodienes, synthesized through a diastereoselective double ring-closing metathesis (DSRCM) reaction, was achieved with good yields (approximately 80%) and excellent enantioselectivities (up to 99% ee). Three contiguous stereocenters are established in a single desymmetrization reaction. The use of thallium carbonate as base in the asymmetric Heck reaction favours double bond migration in 13. Cationic conditions delivered products with good to excellent enantioselectivities, surpassing the results under neutral conditions.
ACCESSION #
12556665

 

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