Saha, Amrita ; Bhattacharyya, Aditya ; Talukdar, Ranadeep ; Ghorai, Manas K. (2018) Stereospecific Syntheses of Enaminonitriles and β-Enaminoesters via Domino Ring-Opening Cyclization (DROC) of Activated Cyclopropanes with Pronucleophilic Malononitriles The Journal of Organic Chemistry, 83 (4). pp. 2131-2144. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.7b03033
Related URL: http://dx.doi.org/10.1021/acs.joc.7b03033
Abstract
Two novel synthetic protocols for the syntheses of highly functionalized five-membered carbocyclic enaminonitriles and β-enaminoesters have been developed via domino ring-opening cyclization (DROC) and DROC/decarboxylative tautomerization of activated cyclopropanes with malononitrile pronucleophiles, respectively. Both of the efficient strategies (yield up to 93%) have been generalized with various donor–acceptor and acceptor cyclopropanes as well as with malononitrile derivatives. The stereospecific variants of the two SN2-type DROC strategies have also been developed by employing enantiopure donor–acceptor (DA) cyclopropanes to synthesize the corresponding nonracemic products with excellent stereoselectivities (dr up to >99:1, ee up to >99%).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 117088 |
| Deposited On: | 15 Apr 2021 07:43 |
| Last Modified: | 15 Apr 2021 07:43 |
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