Organocatalytic asymmetric domino Michael-Henry reaction for the synthesis of substituted bicyclo[3.2.1]octan-2-ones

The first organocatalytic asymmetric reaction between 1,4-cyclohexanedione and nitroalkenes has been studied, affording bicyclo[3.2.1]octane derivatives containing four continuous stereogenic centres. The products were obtained through a domino Michael-Henry process as a single diastereoisomer with...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2013-01, Vol.49 (22), p.2219-2221
Main Authors: Tsakos, Michail, Elsegood, Mark R J, Kokotos, Christoforos G
Format: Article
Language:English
Subjects:
Asymmetry
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Catalysis
Crystallography, X-Ray
Derivatives
Models, Molecular
Molecular Structure
Proline - analogs & derivatives
Proline - chemistry
Synthesis
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Summary:The first organocatalytic asymmetric reaction between 1,4-cyclohexanedione and nitroalkenes has been studied, affording bicyclo[3.2.1]octane derivatives containing four continuous stereogenic centres. The products were obtained through a domino Michael-Henry process as a single diastereoisomer with excellent enantioselectivities.
ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc39165e