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

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons58879

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons132915

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

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58809

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

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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: http://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.