The high stereoselectivity of the tandem sequence Diels-Alder reaction : Ireland-Claisen rearrangement starting from substituted O-(E)-buta-1,3-dienyl ketene acetals and cyclic dienophiles
2007
Abstract
A new tandem reaction leads to bicyclic cyclohexene derivatives with complete control of the relative configuration of the four chiral centers formed. The high diastereoselectivity is the consequence of an endo-selective Diels-Alder reaction followed by an Ireland-Claisen rearrangement that proceeds via a boat-like transition state. © Georg Thieme Verlag Stuttgart.
Details
Title
The high stereoselectivity of the tandem sequence Diels-Alder reaction : Ireland-Claisen rearrangement starting from substituted O-(E)-buta-1,3-dienyl ketene acetals and cyclic dienophiles
Author(s)
Soldermann, N. ; Velker, J. ; Neels, A. ; Stoeckli-Evans, H. ; Neier, R.
Published in
Synthesis
Volume
15
Issue
15
Pages
2379-2387
Date
2007
ISSN
00397881
Note
422
Other identifier(s)
View record in Scopus
Laboratories
SAMLAB
Record Appears in
Scientific production and competences > STI - School of Engineering > STI Archives > SAMLAB - Sensors, Actuators and Microsystems Laboratory
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2009-05-12