Abstract
AbstractA solvent‐free asymmetric and direct anti‐aldol reaction of aliphatic ketones with aromatic aldehydes catalyzed by recyclable L‐prolineamides and L‐prolinethioamides 3 is studied. The L‐prolinethioamide 3d (5 mol%), derived from L‐Pro and (R)‐1‐aminoindane, is the most efficient catalyst for this process affording the anti‐aldol adducts in high yields with excellent diastereo‐ and enantioselectivities (up to >98/2 dr, up to 98% ee) at 0 °C or room temperature. Prolinethioamide 3d is an effective organocatalyst for the first asymmetric, solvent‐free, intramolecular Hajos–Parrish–Eder–Sauer–Wiechert reaction with comparable or higher levels of enantioselectivity (up to 88% ee) to reported catalysts in organic solvents. Moreover, organocatalyst 3d can be easily recovered and reused by a simple acid/base extraction.
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