Calcium-promoted pictet-spengler reactions of ketones and aldehydes

Journal of Organic Chemistry

Volumn 75, Issue 24, 2010, Pages 8542-8549

  Vanden Eynden, Matthew J ^a   Kunchithapatham, Kamala ^a   Stambuli, James P ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE FORMATION; LEWIS ACID; LEWIS ACID CATALYSTS; PICTET-SPENGLER REACTIONS; TETRAHYDROISOQUINOLINES;

ALDEHYDES; CALCIUM; CATALYSTS; CYCLIZATION;

KETONES;

1,1' DISUBSTITUTED TETRAHYDROISOQUINOLINE; 4 O METHYLDOPAMINE; ALDEHYDE DERIVATIVE; AMINE; CALCIUM BIS 1,1,1,3,3,3 HEXAFLUOROISOPROPOXIDE; CALCIUM DERIVATIVE; EMETINE; GLAUCINE; IMINE; KETONE DERIVATIVE; LEWIS ACID; META TYRAMINE; RADDENAMINE; TETRABENAZINE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; PICTET SPENGLER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SEPARATION TECHNIQUE;

EID: 78650352896     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1019283     Document Type: Article

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38. -1 is observed, which is the characteristic absorbance for ammonium ions and tetrasubstituted amines. By observing this peak, we are presuming that under our reaction conditions the molecules may exist in their zwitterionic form. This form makes for very difficult separation and purification due to the high polarity of the electrostatic interactions within the molecules. In fact, chromatographic separation cannot be achieved without strong eluting conditions as the compounds reside on the baseline. Recrystallization is also an acceptable pathway to obtain the product, but low yields and the compound's ability to retain solvent led us away from this purification method. Therefore, a simple trituration with a low boiling and relatively low polarity solvent such as diethyl ether achieved good yields in most cases, even though this isolation technique is not completely quantitative. Therefore, we observe very high and sometimes even quantitative conversion of starting materials to products, but the chemical properties of these compounds lower the amount of isolated material.
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