Abstract
The undesirable side‐processes responsible for the fast deactivation of primary amino acid derived organocatalysts in asymmetric aldol reactions are identified. A new ionic‐liquid‐supported (S)‐valine‐/(S)‐α,α‐diphenylserinol‐derived catalyst (9) is designed on the basis of these results and exhibits much better recyclability in asymmetric syn‐aldol reactions between hydroxyacetone and aldehydes. Furthermore, this catalyst appeared to be useful for the stereoselective synthesis of the naturally occurring 1(3H)‐isobenzofuran‐1‐one scaffold through an asymmetric syn‐aldol/lactonization cascade reaction.
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