Secondary amine catalyzed retro-aldol reactions of enals and enones: One-pot conversion of enals to α-substituted derivatives

Tetrahedron Letters

Volumn 53, Issue 16, 2012, Pages 2091-2095

  Enders, Dieter ^a   Nguyen, Thanh V ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

, Unsaturated aldehydes; Cinnamaldehyde; Iminium activation; Organocatalysis; Retro aldol

Indexed keywords

ALDEHYDE DERIVATIVE; ALKYL GROUP; AMINE; AROMATIC COMPOUND; CINNAMALDEHYDE DERIVATIVE; KETONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ALDOL REACTION; ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHEMICAL BOND; HYDROLYSIS; REACTION ANALYSIS;

EID: 84858438843     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.02.039     Document Type: Article

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15. See for example Ref. 1,3,4,12 on the hydrolysis using organic compounds such as cyclodextrin, proline and glycine as reagents or catalysts. However, these examples either involve the use of inorganic Brønsted bases or are ineffective. On the other hand, there have been several literature examples describing organocatalyzed retro-aldol reactions of β-hydroxy carbonyl compounds: Flock, A. M.; Reucher, C. M. M.; Bolm, C. Chem. Eur. J. 2010, 16, 3918-3921;
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