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Asymmetric Carbolithiation of Conjugated Enynes: A Flow Microreactor Enables the Use of Configurationally Unstable Intermediates before They Epimerize

We found that a flow microreactor system enables the generation of a configurationally unstable chiral organolithium intermediate and allows for its use in a reaction with an electrophile before it epimerizes. Based on this method, the enantioselective carbolithiation of conjugated enynes followed b...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-03, Vol.133 (11), p.3744-3747
Main Authors: Tomida, Yutaka, Nagaki, Aiichiro, Yoshida, Jun-ichi
Format: Article
Language:English
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Summary:We found that a flow microreactor system enables the generation of a configurationally unstable chiral organolithium intermediate and allows for its use in a reaction with an electrophile before it epimerizes. Based on this method, the enantioselective carbolithiation of conjugated enynes followed by the reaction with electrophiles was accomplished to obtain enantioenriched chiral allenes.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja110898s