Asymmetric organocatalytic Michael-type reaction of phosphorus ylides to nitroolefins: synthesis of γ-nitro-β-aryl-α-methylene carboxylic esters

✍ Scribed by Suresh Allu; Sermadurai Selvakumar; Vinod K. Singh

• Book ID: 104097167
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 288 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.11.063

✦ Synopsis

We report, for the first time, asymmetric organocatalytic Michael-type addition of stabilized phosphorus ylides to nitroolefins mediated by bisthiourea catalyst. Its subsequent reaction with formaldehyde provides c-nitro-a-methylene carboxylic esters in moderate to good yields and enantioselectivities (up to 63% ee).