Enantioselective, organocatalytic Morita-Baylis-Hillman and Aza-Morita-Baylis-Hillman reactions: stereochemical issues.
作者： Javier Mansilla , José M. Saá
DOI: 10.3390/MOLECULES15020709
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摘要: Conscious of the importance that stereochemical issues may have on design efficient organocatalyts for both Morita-Baylis-Hillman and aza-Morita-Baylis-Hillman reaction we analyzed them in this minireview. The so-called standard reactions involve “naked” enolates which therefore should lead to syn adducts as major products, irrespective E, Z stereochemistry enolate. Accordingly, provided second step is rate determining step, successful bifunctional or polyfunctional catalysts has consider geometrical requirements imposed by transition structures these reactions. On other hand, MBH aza-MBH co-catalyzed (S)-proline a secondary tertiary amine (co-catalyst) aldol-type condensation either 3-amino-substituted enamine, dienamine, both, depending cases. A Zimmerman-Traxler mechanism defines regarding condensations parallel those well established catalyzed aldol-like
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