Bhattacharyya, Aditya ; Kavitha, C. V. ; Ghorai, Manas K. (2016) Stereospecific Synthesis of 2-Iminothiazolidines via Domino Ring-Opening Cyclization of Activated Aziridines with Aryl- and Alkyl Isothiocyanates Journal of Organic Chemistry, 81 (15). pp. 6433-6443. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.6b01551
Related URL: http://dx.doi.org/10.1021/acs.joc.6b01551
Abstract
Lewis acid-catalyzed domino ring-opening cyclization of activated aziridines with aryl- and alkyl isothiocyanates has been accomplished leading to the formation of a wide variety of highly substituted and functionalized 2-iminothiazolidines with excellent diastereo- and enantiospecificity (de, ee up to >99%). The reaction proceeds via a Lewis acid-catalyzed SN2-type ring-opening of the activated aziridine followed by a concomitant 5-exo-dig cyclization in a domino fashion to furnish the 2-iminothiazolidine derivative in excellent yields (up to 99%).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 117266 |
| Deposited On: | 15 Apr 2021 10:33 |
| Last Modified: | 15 Apr 2021 10:33 |
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