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-acylTEMTOs remained intact, is achieved with these reagents, giving the correspond...

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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 4; pp. 537 - 539
Main Authors Inokuchi, T, Kawafuchi, H, Nokami, J
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.01.2005
Subjects
Alkylating Agents - chemistry
Amides - chemistry
Chemistry
Chemistry, Multidisciplinary
Cyclic N-Oxides - chemistry
Drug Stability
Indicators and Reagents
Metals, Alkali - chemistry
Methanol - chemistry
Molecular Structure
Physical Sciences
Piperidines - chemistry
Science & Technology
KETENES
TEMPO
REDUCTION
LIALH4
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Summary: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-acylTEMTOs remained intact, is achieved with these reagents, giving the corresponding carbinols, respectively.
ISSN:1359-7345
1364-548X
DOI:10.1039/b414129f