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Lewis Acid Mediated [2,3]-Sigmatropic Rearrangement of Allylic Ammonium Ylides
KTH, Superseded Departments, Chemistry.
2003 (English)Licentiate thesis, comprehensive summary (Other scientific)
Abstract [en]

This thesis describes a Lewis acid mediated[2,3]-sigmatropic rearrangement of various allylic ammoniumylides. Several Lewis acids are investigated and BBr3 and BF3are established to be the Lewis acids providing the highestconversion of the starting allylic amines. The observeddiastereoselectivities for (E)-crotyl and (E)-cinnamyl amineare excellent and a transition state model is proposed toaccount for the observed selectivities. The structures of theintermediate Lewis acid-allylic amine complexes are confirmedby NMR spectroscopy studies and a plausible transition state ispresented based on DFT calculations.

As anextension of this investigation, preliminary resultsfrom an asymmetric [2,3]-sigmatropic rearrangement of allylicammonium ylides employing a chiral cyclic bromoborane arepresented.

Place, publisher, year, edition, pages
Stockholm: Kemi , 2003. , 33 p.
Keyword [en]
Sigmatropic rearrangement, Lewis acid, Ammonium ylide, NMR spectroscopy, Density functional calculations
URN: urn:nbn:se:kth:diva-1597ISBN: 91-7283-534-6OAI: diva2:7523
NR 20140805Available from: 2003-08-26 Created: 2003-08-26Bibliographically approved

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