Sankar, Ulaganathan ; Surya Kumar, Ch. Venkata ; Subramanian, V. ; Balasubramanian, K. K. ; Mahalakshimi, S. (2016) 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 The Journal of Organic Chemistry, 81 (6). pp. 2340-2354. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b0284...
Related URL: http://dx.doi.org/10.1021/acs.joc.5b02845
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 107088 |
| Deposited On: | 01 Dec 2017 12:37 |
| Last Modified: | 01 Dec 2017 12:37 |
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