Asymmetric [2,3]-Sigmatropic Rearrangement of Allylic Ammonium Ylides

An asymmetric Lewis acid-mediated [2,3]-sigmatropic rearrangement of allylic amines has been developed, affording the corresponding homoallylic amines in good yield and excellent enantioselectivities. The rearrangement proceeds by complexation of the chiral Lewis acid to the amine followed by deprot...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-07, Vol.127 (26), p.9352-9353
Main Authors: Blid, Jan, Panknin, Olaf, Somfai, Peter
Format: Article
Language:English
Subjects:
allyl compound
ammonium derivative
Chemistry
chirality
diastereoisomer
Exact sciences and technology
Kemi
NATURAL SCIENCES
NATURVETENSKAP
Organic chemistry
quantum yield
reaction analysis
stereochemistry
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Summary:An asymmetric Lewis acid-mediated [2,3]-sigmatropic rearrangement of allylic amines has been developed, affording the corresponding homoallylic amines in good yield and excellent enantioselectivities. The rearrangement proceeds by complexation of the chiral Lewis acid to the amine followed by deprotonation and rearrangement.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja0510562