Reactivity of N-alkanoyloxy-2,2,6,6-tetramethylpiperidines (O-acylTEMPOs) towards hydride-transferring or metallic alkylating reagents; unprecedented stability and application to chemoselective transformations.
Owing to the unprecedented stability of O-acylTEMPOs towards hydride-transferring and metallic alkylating reagents such as LiAlH4 and RMgX, chemoselective transformation of diacid mixed alkyl/TEMP-1-yl esters, where O-acylTEMPOs remained intact, is achieved with these reagents, giving the corresponding carbinols, respectively.
Inokuchi
Tsutomu
T
Department of Bioscience and Biotechnology, Faculty of Engineering, Okayama University, Tsushima-naka, Okayama 700-8530, Japan. inokuchi@cc.okayama-u.ac.jp
Kawafuchi
Hiroyuki
H
Nokami
Junzo
J
D000477:Alkylating Agents / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000737:chemistry*; D004355:Drug Stability; D007202:Indicators and Reagents; D008672:Metals, Alkali / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*
D000477:Alkylating Agents; D000577:Amides; D003497:Cyclic N-Oxides; D007202:Indicators and Reagents; D008672:Metals, Alkali; D010880:Piperidines; C003959:TEMPO; D000432:Methanol