Asymmetric Organocatalytic 1, 4‐Addition Reactions Starting from Enals with gem‐Difluoroalkyl Side Chains. Issue 4 (19th December 2012)

• Record Type: Journal Article
• Authors: Khalaf, Ali; Grée, Danielle; Abdallah, Hassan; Jaber, Nada; Hachem, Ali; Grée, René
• Is Part Of: European journal of organic chemistry. Issue 4(2013)
• Page Start: 653
• Page End: 657
• Publication Date: 2012-12-19
• Subjects: Asymmetric synthesis -- Organo­catalysis -- Michael addition -- Fluorine -- Enals­; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201427
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: gem ‐Difluoroenals are excellent substrates for asymmetric organocatalytic 1, 4‐additions of thiols and anilines. By using diarylsilylprolinol ether as a catalyst, good to excellent yields with ee values in the same range (up to 98 %) were obtained. The CF2 R group strongly activates the enals towards these organocatalytic additions. Abstract : New chiral β‐thio and β‐amino aldehydes with CF2 R chains can be obtained in high yields with high ee values by asymmetric organocatalytic processes after selection of the appropriate catalyst and optimization of the reaction conditions.