English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
Add to Basket
  Local TagsRelease HistoryDetailsSummary

Released
Journal Article

Electrophilic Rearrangements of Chiral Amides: A Traceless Asymmetric α-Allylation

MPS-Authors
/persons/resource/persons58879

Peng,  Bo
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons132915

Geerdink,  Danny
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58809

Maulide,  Nuno
Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource
No external resources are shared
Fulltext (restricted access)
There are currently no full texts shared for your IP range.
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)
There is no public supplementary material available
Citation

Peng, B., Geerdink, D., & Maulide, N. (2013). Electrophilic Rearrangements of Chiral Amides: A Traceless Asymmetric α-Allylation. Journal of the American Chemical Society, 135(40), 14968-14971. doi:10.1021/ja408856p.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A39D-F
Abstract
A one-pot protocol for the asymmetric α-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched α-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.