Abstract
γ− and δ-Oxoesters are easily available starting materials that have been sparingly used in some organocatalyzed reactions proceeding with a high enantioselectivity. In our experimentation we found that the use of these compounds as the enolizable (nucleophilic) component in organocatalyzed Mannich-type reactions using in situ-generated cyclic N-acyl iminium ions gave low diastereoselectivity and low to moderate values of enantioselectivity. This significant drop of facial selectivity with respect to simple aliphatic aldehydes has been rationalized by means of density functional theory (DFT) calculations.
Highlights
Difunctionalized compounds such δ- and γ-oxoesters 1a,b have been widely used in Difunctionalized compounds such δ- and γ-oxoesters 1a,b have been widely used in organic organic synthesis due to their rich chemistry (Figure 1)
The exploitation of the reactivity exploitation of the reactivity of aldehyde functionality of alkyl 5-oxopentanoates has of aldehyde functionality of alkyl 5-oxopentanoates has been exploited in the synthesis of d,l-biotin [1]
Studies using cooperative dualofcatalysis had observedand that the metal catalysts, have been recently developed with aliphatic and α,β-unsaturated combination with different Lewis or Bronsted acids influenced to some extent the reactivity and aldehydes by our research group ourreactions experience inaliphatic this field,aldehydes we have gave stereoselectivity depending on the substrate used.Since
Summary
Difunctionalized compounds such δ- and γ-oxoesters 1a,b have been widely used in Difunctionalized compounds such δ- and γ-oxoesters 1a,b have been widely used in organic organic synthesis due to their rich chemistry (Figure 1). 5-oxopentanoates have been frequently used in (HEW)-olefinations to give a variety of biologically active natural products [2,3,4,5,6,7,8,9]. Notwithstanding the Horner-Wadsworth-Emmons (HEW)-olefinations to give a variety of biologically active increasing importance of organocatalysis in modern synthetic organic chemistry and the large variety natural products [2,3,4,5,6,7,8,9]. Notwithstanding the increasing importance of organocatalysis in of reactions described, the use of oxoesters in organocatalyzed reactions has not been considered modern synthetic organic chemistry and the large variety of reactions described, the use to a large extent. For component in secondary amine-organocatalyzed Michael-type [10,11,12,13] and aldol reactions [14], all Molecules
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