Please use this identifier to cite or link to this item:
http://hdl.handle.net/2445/45524
Title: | Comparing and taming the reactivity of HWE and Wittig reagents with cyclic hemiacetals |
Author: | Carrillo Arregui, Jokin Costa i Arnau, Anna M. Sidera Portela, Mireia Vilarrasa i Llorens, Jaume |
Keywords: | Química orgànica Reactivitat (Química) Nomenclatura química Síntesi orgànica Organic chemistry Reactivity (Chemistry) Chemical nomenclature Organic synthesis |
Issue Date: | 2011 |
Publisher: | Elsevier Ltd |
Abstract: | A practical solution to the formation of mixtures of E/Z and open/cyclic isomers in the reaction of (2R,4S)-4-hydroxy-2-methylpentanal (as its hemiacetal, a lactol) with conjugated phosphoranes (stabilised Wittig reagents) and Horner-Wadsworth-Emmons reagents is disclosed. The HWE reaction has a strong bias to give oxolanes. On the other hand, stabilised Wittig reagents give unsaturated carboxyl derivatives of configuration E (major) and oxolanes (minor); the latter can be avoided by addition of CF3CH2OH or using morpholine amide phosphorane. |
Note: | Versió postprint del document publicat a: http://dx.doi.org/10.1016/j.tetlet.2011.07.121 |
It is part of: | Tetrahedron Letters, 2011, vol. 52, num. 40, p. 5153-5156 |
URI: | http://hdl.handle.net/2445/45524 |
Related resource: | http://dx.doi.org/10.1016/j.tetlet.2011.07.121 |
ISSN: | 0040-4039 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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