title: C-H functionalization of terminal alkynes towards stereospecific synthesis of (E) or (Z) 2-methylthio-1,4-ene-diones.
abstract: An efficient metal free self-sorting tandem protocol for stereospecific synthesis of 2-thio-1,4-enediones involving C-C double bond formation via direct coupling of terminal alkynes has been developed. The method was also extended to the first synthesis of β-thio-γ-keto-α,β-unsaturated esters via a cross coupling reaction with ethyl glyoxylate. The reaction relies on a first of its kind use of Bronsted and Lewis acids to switch selectivity for the synthesis of an E or a Z-isomer respectively.
authors.affiliation: Academy of Scientific and Innovative Research (AcSIR), Natural Product Microbes, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu-Tawi, 180001, India. bashah@iiim.ac.in.
authors.forename: Shekaraiah
authors.initials: S
authors.lastname: Devari
authors.forename: Arvind
authors.initials: A
authors.lastname: Kumar
authors.forename: Ramesh
authors.initials: R
authors.lastname: Deshidi
authors.forename: Bhahwal Ali
authors.initials: BA
authors.lastname: Shah
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002074:Butanones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D002074:Butanones; D013440:Sulfides