Bhattacharyya, Aditya ; Shahi, Chandan Kumar ; Pradhan, Sajan ; Ghorai, Manas K. (2018) Stereospecific Synthesis of 1,4,5,6-Tetrahydropyrimidines via Domino Ring-Opening Cyclization of Activated Aziridines with α-Acidic Isocyanides Organic Letters, 20 (10). pp. 2925-2928. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/acs.orglett.8b00986
Related URL: http://dx.doi.org/10.1021/acs.orglett.8b00986
Abstract
An expeditious synthetic route to access structurally diverse 1,4,5,6-tetrahydropyrimidines via domino ring-opening cyclization of activated aziridines with α-acidic isocyanides has been established. The transformation proceeds via Lewis acid mediated SN2-type ring opening of activated aziridines with α-carbanion of the isocyanides followed by a concomitant 6-endo-dig cyclization in a domino fashion to furnish the 1,4,5,6-tetrahydropyrimidine derivatives in excellent yields (up to 84%) and also in diastereo- and enantiomerically pure form (dr >99:1, ee >99%).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 117086 |
| Deposited On: | 15 Apr 2021 07:43 |
| Last Modified: | 15 Apr 2021 07:43 |
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