research article
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
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.
Type
research article
Scopus ID
2-s2.0-34547749424
Author(s)
Soldermann, N.
Velker, J.
Neels, A.
Stoeckli-Evans, H.
Neier, R.
Date Issued
2007
Publisher
Published in
Volume
15
Issue
15
Start page
2379
End page
2387
Note
422
Editorial or Peer reviewed
REVIEWED
Written at
OTHER
EPFL units
Available on Infoscience
May 12, 2009
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