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

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.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0014-A39D-F Version Permalink: http://hdl.handle.net/11858/00-001M-0000-001A-153C-0
Genre: Journal Article

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 Creators:
Peng, Bo1, Author              
Geerdink, Danny1, Author              
Maulide, Nuno1, Author              
Affiliations:
1Research Group Maulide, Max-Planck-Institut für Kohlenforschung, Max Planck Society, escidoc:1445614              

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 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.

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Language(s): eng - English
 Dates: 2013-09-30
 Publication Status: Published online
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1021/ja408856p
 Degree: -

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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: -
Pages: - Volume / Issue: 135 (40) Sequence Number: - Start / End Page: 14968 - 14971 Identifier: ISSN: 0002-7863
CoNE: http://pubman.mpdl.mpg.de/cone/journals/resource/954925376870