Asymmetric Mannich reaction catalyzed by N-arylsulfonyl- l-proline amides

Proline-derived N-sulfonylcarboxamides efficiently catalyze the asymmetric Mannich reaction of cyclic ketones with N-( p-methoxyphenyl)-protected iminoglyoxylate. Both classical organic solvents and ionic liquids were used as the reaction media. With cyclohexanone, the reaction proceeded with high e...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 21; no. 1; pp. 58 - 61
Main Authors Veverkova, Eva, Strasserova, Jana, Sebesta, Radovan, Toma, Stefan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.01.2010
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
N-(P-DODECYLPHENYLSULFONYL)-2-PYRROLIDINECARBOXAMIDE
MICHAEL
SCOPE
IMINES
ORGANOCATALYSIS
ENANTIOSELECTIVE ALDOL REACTIONS
IONIC LIQUIDS
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Summary:Proline-derived N-sulfonylcarboxamides efficiently catalyze the asymmetric Mannich reaction of cyclic ketones with N-( p-methoxyphenyl)-protected iminoglyoxylate. Both classical organic solvents and ionic liquids were used as the reaction media. With cyclohexanone, the reaction proceeded with high enantioselectivity (99% ee). Enamine intermediates were investigated by DFT calculations.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2009.12.013