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 inJournal of the American Chemical Society Vol. 133; no. 11; pp. 3744 - 3747
Main Authors Tomida, Yutaka, Nagaki, Aiichiro, Yoshida, Jun-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.03.2011
Amer Chemical Soc
Subjects
Alkenes - chemistry
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Stereoisomerism
CARBON BOND FORMATION
ORGANIC-SYNTHESIS
REACTOR
DYNAMIC THERMODYNAMIC RESOLUTION
FLASH CHEMISTRY
MICROFLOW SYSTEM
KINETIC RESOLUTION
SYNTHETIC APPLICATIONS
CHIRAL ORGANOLITHIUM COMPOUNDS
LITHIATION-SUBSTITUTION SEQUENCES
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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.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja110898s