Calcium-Promoted Pictet-Spengler Reactions of Ketones and Aldehydes

Calcium bis-1,1,1,3,3,3-hexafluoroisopropoxide is shown to be an effective catalyst for Pictet−Spengler reactions of 3-hydroxyphenethylamine and 3-hydroxy-4-methoxyphenethylamine with various aldehydes and ketones. Previous Lewis acid catalyzed Pictet−Spengler reactions of unactivated ketones typica...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-12, Vol.75 (24), p.8542-8549
Main Authors: Vanden Eynden, Matthew J, Kunchithapatham, Kamala, Stambuli, James P
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Calcium bis-1,1,1,3,3,3-hexafluoroisopropoxide is shown to be an effective catalyst for Pictet−Spengler reactions of 3-hydroxyphenethylamine and 3-hydroxy-4-methoxyphenethylamine with various aldehydes and ketones. Previous Lewis acid catalyzed Pictet−Spengler reactions of unactivated ketones typically require two separate reactions (imine formation, cyclization) to obtain the same results. The reactions described within directly provide 1,1′-disubstituted tetrahydroisoquinolines from the corresponding amine and ketone. These rare examples of Pictet−Spengler reactions of unactivated ketones demonstrate the unique nature of calcium as a Lewis acid catalyst.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo1019283