title: Stereo-, Regio-, and Chemoselective [3 + 2]-Cycloaddition of (2E,4E)-Ethyl 5-(Phenylsulfonyl)penta-2,4-dienoate with Various Azomethine Ylides, Nitrones, and Nitrile Oxides: Synthesis of Pyrrolidine, Isoxazolidine, and Isoxazoline Derivatives and a Computational Study.
abstract: One-pot chemo-, regio-, and stereoselective synthesis of series of heterocyclic and spiroheterocyclic compounds was accomplished through mono- and bis[3 + 2]-cycloaddition reactions of (2E,4E)-ethyl 5-(phenylsulfonyl)penta-2,4-dienoate as a dipolarophile with azomethine ylides, nitrones, and nitrile oxides in good yields. The structures of the products were established by spectroscopic techniques as well as by single-crystal XRD study, and DFT calculations were performed to further understand the mechanism of this [3 + 2]-cycloaddition reaction.
authors.affiliation: Department of Chemistry, Pachaiyappa's College, University of Madras , Chennai 600030, India.
authors.forename: Ulaganathan
authors.initials: U
authors.lastname: Sankar
authors.affiliation: Chemical Laboratory, CSIR-Central Leather Research Institute , Adyar, Chennai 600020, India.
authors.forename: Ch Venkata
authors.initials: ChV
authors.lastname: Surya Kumar
authors.affiliation: Chemical Laboratory, CSIR-Central Leather Research Institute , Adyar, Chennai 600020, India.
authors.forename: V
authors.initials: V
authors.lastname: Subramanian
authors.affiliation: INSA Senior Scientist, Department of Chemistry, Indian Institute of Technology Madras , Chennai 600020, India.
authors.forename: K K
authors.initials: KK
authors.lastname: Balasubramanian
authors.affiliation: Department of Chemistry, Pachaiyappa's College, University of Madras , Chennai 600030, India.
authors.forename: S
authors.initials: S
authors.lastname: Mahalakshimi