Control of aldol reaction pathways of enolizable aldehydes in an aqueous environment with a hyperbranched polymeric catalyst

Journal of the American Chemical Society

Volumn 130, Issue 51, 2008, Pages 17287-17289

  Chi, Yonggui ^a   Scroggins, Steven T ^a   Boz, Emine ^a   Fré Chet, Jean M J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL CONDENSATION; ALDOL REACTIONS; AQUEOUS ENVIRONMENT; CATALYTIC CONDITIONS; CATALYTIC PROCESS; CHEMO-SELECTIVITY; CONTROL EXPERIMENTS; EFFICIENT SYNTHESIS; HYPERBRANCHED; MECHANISTIC STUDIES; POLYETHYLENEIMINE; POLYMER CATALYSTS; POLYMERIC CATALYSTS; POTENTIAL APPLICATIONS; SMALL MOLECULES; UNSATURATED KETONES;

ALDEHYDES; CATALYSIS; CATALYSTS; CONDENSATION; DENDRIMERS; KETONES; POLYMERS; UNSATURATED POLYMERS;

CONDENSATION REACTIONS;

ALDEHYDE; KETONE; POLYMER;

ALDOL REACTION; AQUEOUS SOLUTION; ARTICLE; CATALYST; CONTROLLED STUDY; MANNICH REACTION; POLYMERIZATION; REACTION TIME; STEREOCHEMISTRY;

EID: 67849126360     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806584q     Document Type: Article

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33. 1H NMR analysis of the crude reaction mixture (see the SI). Isolated yields after column chromatography are in the range 50% to 80% for 11c and 11h.
34. For example, in a scalable preparation of 11c and 11h (Scheme 4), distillation yielded a mixture with two separate layers: an organic layer containing the desired product in high purity and a water layer. The white solid residue remaining after distillation contains the catalyst, which was directly reused without purification, showing only a slight loss in catalytic activity.