Organocatalyzed Michael Addition Reaction by Novel (2R,3aS,7aS)-Octahydroindole-2-carboxylic Acid, a New Fused Proline

We present here the results obtained in our study on organocatalytic enantioselective Michael addition reaction of acetone to different nitroolefines using (2R,3aS,7aS)-octahydroindole-2-carboxylic acid [(R,S,S)-Oic] as a new and suitable catalyst for this process. Computational calculations support...

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Bibliographic Details
Published inSynlett no. 2; pp. 249 - 253
Main Authors Roca-Lopez, David, Merino, Pedro, Sayago, Francisco J., Cativiela, Carlos, Herrera, Raquel P.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 11.01.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
enantioselectivity
HEREDITARY ANGIOEDEMA
Oic
CARBONYL-COMPOUNDS
ALDEHYDES
CATALYST
ketones
organocatalysis
FUNCTIONALIZATION
nitroolefines
ASYMMETRIC MICHAEL
NITRO
CONJUGATE ADDITION
RATIONAL DESIGN
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Summary:We present here the results obtained in our study on organocatalytic enantioselective Michael addition reaction of acetone to different nitroolefines using (2R,3aS,7aS)-octahydroindole-2-carboxylic acid [(R,S,S)-Oic] as a new and suitable catalyst for this process. Computational calculations support the results obtained with (R, S, S)-Oic versus its diastereomeric form (S, S, S)-Oic. The final products are obtained in good yields and moderate enantioselectivities (up to 58% ee).
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1259296