title: Enantioselective synthesis of γ-tetrasubstituted nitrosulfonyl carboxylates and amides via L-tert-leucine-derived-squaramide catalyzed conjugate addition of nitrosulfones to acrylates and acrylamides.
abstract: Michael addition of α-nitrosulfones to aryl- and alkyl acrylates and acrylamides proceeds in the presence of 5-10 mol% of an amino acid derived new organocatalyst to provide γ-tetrasubstituted γ-nitro-γ-sulfonyl carboxylates and amides in excellent yields and enantioselectivities. Scale-up of the reaction to multi-grams, convenient recovery of the catalyst and its recyclability without any drop in yield and selectivity are attractive features of this methodology.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India. irishi@iitb.ac.in.
authors.forename: Kalisankar
authors.initials: K
authors.lastname: Bera
authors.forename: Irishi N N
authors.initials: IN
authors.lastname: Namboothiri
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D007930:Leucine / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000179:Acrylates; D000577:Amides; D002264:Carboxylic Acids; D007930:Leucine