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The direct formation of alpha-methylene-beta-amino acid derivatives is achieved using the aza version of the Baylis-Hillman protocol. The products are readily formed in a three-component one-pot reaction between arylaldehydes, sulfonamides, and alpha,beta-unsaturated carbonyl compounds. The reaction is efficiently catalyzed by titanium isopropoxide and 2-hydroxyquinuclidine in the presence of molecular sieves. The protocol allows for structural variation of the substrates, tolerating electron-poor and electron-rich arylaldehydes and various Michael acceptors.

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Enantioselective synthesesEnantioselective syntheses O 0031 Chiral Quinuclidine-Based Amine Catalysts for the Asymmetric One-Pot, Three-Component Aza-Baylis-Hillman Reaction. -The quinidine derivative (I) is used as an efficient catalyst for the title reaction. -(BALAN, D.; ADOLFSSON*, H.; Tetrahedron Lett. 44 (2003) 12, 2521-2524; Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.; Eng.) -Roy 26-040