Exploring the versatility of the Johnson-Claisen rearrangement: Access to functionally versatile delta-ethoxycarbonyl-alpha,beta-unsaturated nitriles

Cosgrove, Kelly L. and McGeary, Ross P. (2010) Exploring the versatility of the Johnson-Claisen rearrangement: Access to functionally versatile delta-ethoxycarbonyl-alpha,beta-unsaturated nitriles. Tetrahedron, 66 16: 3050-3057. doi:10.1016/j.tet.2010.02.045


Author Cosgrove, Kelly L.
McGeary, Ross P.
Title Exploring the versatility of the Johnson-Claisen rearrangement: Access to functionally versatile delta-ethoxycarbonyl-alpha,beta-unsaturated nitriles
Formatted title
Exploring the versatility of the Johnson-Claisen rearrangement: access to functionally versatile δ-ethoxycarbonyl-α,β-unsaturated nitriles
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
1464-5416
Publication date 2010-04-01
Sub-type Article (original research)
DOI 10.1016/j.tet.2010.02.045
Volume 66
Issue 16
Start page 3050
End page 3057
Total pages 8
Place of publication Oxford, U.K.
Publisher Pergamon Press
Collection year 2011
Language eng
Formatted abstract
A practical entry into δ-ethoxycarbonyl-α,β-unsaturated nitriles is described. α,β-Unsaturated aldehydes were converted to cyanohydrins, by employing either KCN in aqueous acid, or by using TMSCN with catalytic K2CO3, followed by acid hydrolysis of the TMS ether. These cyanohydrins underwent a Claisen rearrangement employing a modified Johnson–Claisen protocol to yield unsaturated nitriles in good yields and with moderate E/Z selectivity.
© 2010 Elsevier Ltd. All rights reserved.
Keyword Johnson-Claisen rearrangement
Cyanohydrins
Unsaturated nitriles
Allylic alcohols
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2011 Collection
School of Chemistry and Molecular Biosciences
School of Pharmacy Publications
 
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Created: Sun, 02 May 2010, 10:00:55 EST