Triflimide-catalysed sigmatropic rearrangement of N-allylhydrazones as an example of a traceless bond construction
- 28 February 2010
- journal article
- research article
- Published by Springer Nature in Nature Chemistry
- Vol. 2 (4) , 294-297
- https://doi.org/10.1038/nchem.576
Abstract
A triflimide-catalysed rearrangement of N-allylhydrazones has been developed that allows for the generation of a sigma bond between two unfunctionalized sp3 carbons such that no clear marker remains for how the bond was formed. This traceless bond construction offers new avenues for convergent fragment coupling in synthetic strategies.Keywords
This publication has 16 references indexed in Scilit:
- Metal-free carbon–carbon bond-forming reductive coupling between boronic acids and tosylhydrazonesNature Chemistry, 2009
- Stereoselective Synthesis of Dienes from N-AllylhydrazonesOrganic Letters, 2008
- Tandem Carbon−Carbon and Carbon−Chlorine Bond Formation by Cu(II) Chloride-Promoted [3,3] Sigmatropic Rearrangement of N-AllylhydrazonesJournal of the American Chemical Society, 2008
- Stronger Brønsted AcidsChemical Reviews, 2007
- Claisen Rearrangement over the Past Nine DecadesChemical Reviews, 2004
- Synthesis of (+)-CP-263,114Journal of the American Chemical Society, 2000
- Highly Efficient Methodology for the Reductive Coupling of Aldehyde Tosylhydrazones with Alkyllithium ReagentsJournal of the American Chemical Society, 1998
- Stereoselective synthesis of olefins from silylated sulfonylhydrazonesJournal of the American Chemical Society, 1990
- The preparation of hindered cuprates from aldehyde tosylhydrazonesTetrahedron Letters, 1980
- Reductive alkylation of aldehyde tosylhydrazones with organolithium reagentsTetrahedron Letters, 1977