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Synlett 2015; 26(09): 1248-1252
DOI: 10.1055/s-0034-1380382
DOI: 10.1055/s-0034-1380382
letter
Asymmetric Conjugate Addition of Ketones to Maleimides Using Diaminomethyleneindenedione Organocatalyst
Further Information
Publication History
Received: 29 January 2015
Accepted after revision: 22 February 2015
Publication Date:
19 March 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201509/lookinside/thumbnails/st-2015-u0069-l_10-1055_s-0034-1380382-1.jpg)
Abstract
A novel diaminomethyleneindenedione (DMI) organocatalyst efficiently promotes the asymmetric conjugate addition of a ketone to a maleimide to afford the corresponding addition product in a high yield with up to 99% enantiomeric excess.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380382.
- Supporting Information
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References and Notes
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- 14 Typical Procedure of the Conjugate Additions to Maleimides Using 3 To a mixture of N-phenylmaleimide (4a, 34.6 mg, 0.200 mmol) and acetone (73.4 μL, 1.00 mmol) in p-xylene (0.4 mL) was added organocatalyst 3 (20.5 mg, 0.040 mmol) and benzoic acid (2.5 mg, 0.020 mmol) at r.t. After stirring in closed tube at 40 °C for 48 h, the reaction mixture was directly purified by flash column chromatography on silica gel with a 3:2 to 1:1 mixture of hexane and EtOAc to afford 5a (37.3 mg, 81%) as a white powder.
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