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Synlett 2014; 25(13): 1863-1868
DOI: 10.1055/s-0034-1378274
DOI: 10.1055/s-0034-1378274
letter
Nucleophilic Addition Reactions of Nitriles to Nitrones under Mild Silylation Conditions
Further Information
Publication History
Received: 09 April 2014
Accepted after revision: 07 May 2014
Publication Date:
24 June 2014 (online)
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Abstract
In the presence of triethylsilyl trifluoromethanesulfonate and triethylamine, aliphatic nitriles undergo addition reactions with aldonitrones under non-basic, mild conditions, providing O-triethylsilyl ethers of β-N-hydroxyamino nitriles with high yield. The reaction appears to proceed through formation of an N-silyl ketene imine in situ followed by a Mannich-type reaction.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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References and Notes
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- 19 General Procedure (Table 1, entry 6): To a mixture of nitrone 10 (0.4 mmol), nitrile 13 (0.4 mmol), and Et3N (0.8 mmol) in DCE (2 mL), was added TESOTf (0.8 mmol) at –30 °C, and the reaction mixture was stirred at this temperature for 30 min. Sat. aq sodium bicarbonate (1 mL) was added to the mixture, and the product was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2; hexane–Et2O, 15:1) afforded O-TES β-hydroxyamino nitrile 14c (0.377 mmol, 94%).
For reviews, see:
For typical examples, see:
For related aziridinations, see: