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Catalyst-free Mannich-type reaction of 1-(N-acylamino)alkyltriphenylphosphonium salts with silyl enolates |
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| Authors: | Agnieszka Październiok-Holewa Alicja Walęcka-Kurczyk Szymon Musioł Sebastian Stecko |
| Institution: | 1. Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100, Gliwice, Poland;2. Biotechnology Centre of Silesian University of Technology, B. Krzywoustego 8, 44-100, Gliwice, Poland;3. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland |
| Abstract: | A catalyst-free reaction of 1-(N-acylamino)alkyltriphenylphosphonium tetrafluoroborates with silyl enolates was developed to prepare β-amino carbonyl compounds. The reported method is a useful approach for the preparation of N-protected β-amino esters as well as N-protected β-amino ketones. The starting 1-(N-acylamino)alkyltriphenylphosphonium tetrafluoroborates are readily available from N-protected α-amino acids. Therefore, the presented approach can be considered a new method for the α-homologation of N-protected α-amino acids to prepare β-amino acid derivatives. |
| Keywords: | Mannich-type reaction β-Amino carbonyl compounds Phosphonium salts Silyl enolates Catalyst-free reaction |
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