Asymmetric Deprotonation of N-Boc Piperidine: React IR Monitoring and Mechanistic Aspects

The high yielding asymmetric deprotonation trapping of N-Boc piperidine is successfully realized using s-BuLi and a (+)-sparteine surrogate. Monitoring of the lithiation by in situ React IR allowed the direct observation of a prelithiation complex.

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 132; no. 21; pp. 7260 - 7261
Main Authors Stead, Darren, Carbone, Giorgio, O’Brien, Peter, Campos, Kevin R, Coldham, Iain, Sanderson, Adam
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.06.2010
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Piperidines - chemistry
Protons
Science & Technology
Spectrophotometry, Infrared
Stereoisomerism
LITHIATION
PYRROLIDINE
COMPLEX
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Summary:The high yielding asymmetric deprotonation trapping of N-Boc piperidine is successfully realized using s-BuLi and a (+)-sparteine surrogate. Monitoring of the lithiation by in situ React IR allowed the direct observation of a prelithiation complex.
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja102043e