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Carbamoyl Anion Addition to Nitrones

Jonathan T. Reeves*, Chris Lorenc, Kaddy Camara, Zhibin Li, Heewon Lee, Carl A. Busacca and Chris H. Senanayake

*Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States, Email: jonathan.reevesboehringer-ingelheim.com

J. T. Reeves, C. Lorenc, K. Camara, Z. Li, H. Lee, C. A. Busacca, C. H. Senanayake, J. Org. Chem., 2014, 79, 5895-5902.

DOI: 10.1021/jo500848a



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Abstract

The addition of carbamoyl anions derived from N,N-disubstituted formamides and LDA to N-tert-butyl nitrones provided a direct route to α-(N-hydroxy)amino amides. Derivatization of the products by tert-butyl deprotection or N-deoxygenation was demonstrated.

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Key Words

α-Amino Acid Derivatives


ID: J42-Y2014