Prolinamide‐Derived Ionic‐Liquid‐Supported Organocatalyst for Asymmetric Mono‐ and Bis‐Aldol Reactions in the Presence of Water

Abstract

A novel recyclable prolinamide-derived ionic-liquid-supported organocatalyst of asymmetric cross-aldol reactions in aqueous medium has been developed. In its presence, aromatic aldehydes react with cyclic or linear ketones to afford chiral aldol adducts in moderate to high yields and with ex-

Towards an Understanding of the “Ambiphilic” Character of Ionic Liquids for Green Synthesis of Chemically Diverse Architectures

“…Zlotin et al. reported a recoverable prolinamide‐based ionic‐liquid for asymmetric Aldol condensation between aromatic aldehydes 48 and linear or cyclic ketones 49 in the presence of water (Scheme and Scheme ) . The corresponding Aldol adducts were obtained in moderate to good yields and with excellent dr (anti/syn up to 96 : 4) and ee (81–99%) values which remained unchanged for over ten recycles of the catalyst.…”

Catalytic strategies towards 1,3-polyol synthesis by enantioselective cascades creating multiple alcohol functions

“…26 Finally, the group of Zlotin created a prolinamide-derived ionic-liquid-supported aminocatalyst cat9 performing an efficient reaction in water only with electrondeficient aldehydes. 27 It must be pointed out that in these aminocatalyzed double aldolizations, the second catalyst-controlled reaction is responsible for an amplification of chirality associated with higher enantiocontrol of the double aldolization product than for the corresponding mono-aldolization one. Even though the reaction holds promises for the direct preparation of 1,3-keto-diols, a scaffold found in different natural products, the limited scope and reactivity hamper for now the applicability of this approach.…”

Ionic Liquids in Asymmetric Synthesis: An Overall View from Reaction Media to Supported Ionic Liquid Catalysis

“…In 2015, the same research group designed 72 to eliminate the disadvantages of their previouss ystems such as high catalyst loading and low recyclability in the reaction. [111] This catalysth as been employedi nt he asymmetrica ldol reaction of aromatic aldehydesa nd linear and cyclic ketones in water as the solvent. The corresponding aldol adducts are achieved in moderate to excellent conversionsw ith excellent dr (anti/ syn up to 96:4) and ee (81-99 %) values.…”