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Titanium Isopropoxide as Efficient Catalyst for the Aza-Baylis−Hillman Reaction. Selective Formation of α-Methylene-β-amino Acid Derivatives

2002; American Chemical Society; Volume: 67; Issue: 7 Linguagem: Inglês

10.1021/jo0163952

1520-6904

Daniela Balan, Hans Adolfsson,

Fluorine in Organic Chemistry

The direct formation of α-methylene-β-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 α,β-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.