The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone

The reaction of enals with α,α′-diaryl-substituted acetones (p K a > 18) catalyzed by ( S )-1-(2-pyrrolidinylmethyl) pyrrolidine provides direct access to enantioenriched 2,5,6-trisubstituted-3-hydroxy cyclohexanones. The process constitutes a highly stereoselective organocatalytic tandem Michael...

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Bibliographic Details
Published in:RSC advances 2015-01, Vol.5 (81), p.65975-65981
Main Authors: Guevara-Pulido, James O., Andrés, José M., Pedrosa, Rafael
Format: Article
Language:English
Subjects:
Acetone
Aldehydes
Cascade chemical reactions
Chemical reactions
Cyclohexanone
Derivatives
Synthesis (chemistry)
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Summary:The reaction of enals with α,α′-diaryl-substituted acetones (p K a > 18) catalyzed by ( S )-1-(2-pyrrolidinylmethyl) pyrrolidine provides direct access to enantioenriched 2,5,6-trisubstituted-3-hydroxy cyclohexanones. The process constitutes a highly stereoselective organocatalytic tandem Michael-intramolecular aldol reaction. It has been demonstrated that the stereoselection is dependent on the reaction conditions because only syn diastereoisomers are able to cyclize, and that anti diastereoisomers participate in a retro-Michael process decreasing the enantioselection.
ISSN:2046-2069
2046-2069
DOI:10.1039/C5RA11215J