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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:
It is part of: Tetrahedron Letters, 2011, vol. 52, num. 40, p. 5153-5156
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ISSN: 0040-4039
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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