Titanium Isopropoxide as Efficient Catalyst for the Aza-Baylis−Hillman Reaction. Selective Formation of α-Methylene-β-amino Acid Derivatives
- 13 March 2002
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (7) , 2329-2334
- https://doi.org/10.1021/jo0163952
Abstract
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.Keywords
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