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Organocatalysis by Manfred Reetz, Benjamin List, Stefan Jaroch, Hilmar Weinmann

By Manfred Reetz, Benjamin List, Stefan Jaroch, Hilmar Weinmann

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1 Enzymes as Archetypes . . . . . . . . . . . 2 The Benzoin Condensation . . . . . . . . . . 3 The Stetter Reaction . . . . . . . . . . . . 4 Conclusion . . . . . . . . . . . . . . . References . . . . . . . . . . . . . . . . . 46 . 47 . 47 . 69 . 73 . 75 . . . 82 82 83 104 107 108 Abstract. Mother Nature utilizes simple precursors to build up complex organic molecules efficiently. One important example is the C3 building block dihydroxyacetone phosphate, which is used in various enzyme-catalyzed reactions.

3 First Direct Organocatalytic α-Fluorination of Aldehydes and Ketones . . . . . . . . . . . . . . 4 Asymmetric Organocatalytic Multicomponent Domino Reactions 3 C–C-Bond Formations Employing N-Heterocyclic Carbene Catalysis . . . . . . . . . . . . . . . 1 Enzymes as Archetypes . . . . . . . . . . . 2 The Benzoin Condensation . . . . . . . . . . 3 The Stetter Reaction . . . . . . . . . . . . 4 Conclusion . . . . . . . . .

2003). 1 Asymmetric Counteranion-Directed Catalysis: Application to Iminium Catalysis In iminium catalysis, both we and the group of MacMillan had observed a strong counteranion effect on the yield and enantioselectivity of the reactions. Inspired by recent use of chiral phosphoric acid derivatives Scheme 23. Asymmetric counteranion-directed catalysis: application to iminium catalysis New Concepts for Organocatalysis 29 as asymmetric catalysts, we hypothesized that catalytic salts of achiral amines and chiral phosphoric acids could induce asymmetry in these processes (Scheme 23).

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