Influence of the Reaction Conditions on the Evolution of the Michael Addition of β-Keto Sulfones to α,β-Unsaturated Aldehydes

• Published in: European Journal of Organic Chemistry 2010-08, Vol.2010 (23), p.4482-4491
• Main Authors: Alemán, José, Marcos, Vanesa, Marzo, Leyre, García Ruano, José Luis
• Format: Article
• Language: English
• Subjects: Aldehydes; Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Keto sulfones; Michael addition; Organic chemistry; Organocatalysis; Preparations and properties
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201000502

We have studied the influence of different reaction conditions on the conjugated addition of β‐keto sulfones to α,β‐unsaturated aldehydes catalyzed by silyl prolinol ethers. Small changes in the starting material and/or in the experimental protocol are able to produce significant variations in the structures of the final products. The high chemical versatility of the resulting Michael adducts make possible their use in a variety of tandem and one‐pot reactions to afford polysubstituted cyclic products bearing multiple chiral centers. We have studied the influence of different reaction conditions on the conjugated addition of β‐keto sulfones to α,β‐unsaturated aldehydes catalyzed by silyl prolinol ethers. Small changes in the starting material and/or in the experimental protocol are able to produce significant variations in the structures of the final products.