Complete stereocontrol in organocatalytic additions of β- ketosulfoxides to conjugated aldehydes

Chemistry - A European Journal

Volumn 17, Issue 14, 2011, Pages 4030-4037

  García Ruano, José Luis ^a   Alvarado, Cuauhtémoc ^a   Díaz Tendero, Sergio ^a   Alemán, José ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

chiral auxiliaries; enantioselectivity; Michael addition; organocatalysis; sulfoxides

Indexed keywords

ACTIVE REAGENTS; CARBON ATOMS; CHIRAL AUXILIARIES; CHIRAL CENTERS; COMPLETE CONTROL; CONJUGATED ALDEHYDES; DIASTEREOISOMERS; ELECTROPHILES; ENOLATES; MICHAEL ADDITION; ORGANOCATALYSIS; ORGANOCATALYTIC; PROLINE DERIVATIVES; STEREOCONTROL; SULFINYL GROUP; SULFOXIDES; THEORETICAL CALCULATIONS; UNSATURATED ALDEHYDES;

ADDITION REACTIONS; ALDEHYDES; AMINO ACIDS; ENANTIOSELECTIVITY; FUNCTIONAL GROUPS; NUCLEOPHILES; RATE CONSTANTS; REACTION KINETICS; STEREOCHEMISTRY; SULFUR;

CATALYSIS;

EID: 79952829420     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003267     Document Type: Article

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55. We are aware that the calculations concerning the possible starting reagents only provide limited support for the mechanistic proposal because, according to the Curtin-Hammett principle, the stability of the possible transition states should be considered. To this end, a complete computational study of all the transition states associated with the reactions of the different conformers for the enols and enolates indicated in this manuscript, with the iminium ion leading to the final compound, is in progress. Furthermore, the significant role of the hydrogen bonds in these reactions will also be considered. The results will be published in the due course.
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