The facile preparation of primary and secondary amines via an improved Fukuyama–Mitsunobu procedure. Application to the synthesis of a lung-targeted gene …

…, JE Waterhouse, WS Price, MR Jorgensen…

Index: Guisado, Cristina; Waterhouse, Jodie E.; Price, Wayne S.; Jorgensen, Michael R.; Miller, Andrew D. Organic and Biomolecular Chemistry, 2005 , vol. 3, # 6 p. 1049 - 1057

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Citation Number: 35

Abstract

An efficient modification of the Fukuyama–Mitsunobu procedure has been developed whereby primary or secondary amines can be synthesized from alkyl alcohols and the corresponding nosyl-protected/activated amine. Most importantly, the use of the DTBAD and diphenylpyridinylphosphine, as Mitsunobu reagents, generates reaction by-products that can be easily removed, providing a remarkably clean product mixture. This improved ...