A simple method for coupling aldehydes to solid support

A new method for attaching aldehydes to solid supports has been developed employing a 2,2-bis(hydroxymethyl)propionic acid (DMPA ®) functionalized resin. High loading levels are obtained for both aryl and alkyl aldehydes protected as their respective acetals. Treatment of the derivatized resin with...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1998-09, Vol.8 (17), p.2399-2402
Main Authors: Metz, William A., Jones, Winton D., Ciske, Fred L., Peet, Norton P.
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Carboxylic Acids - chemical synthesis
Carboxylic Acids - chemistry
Chemistry, Organic - methods
Hydroxy Acids
Kinetics
Propionates
Resins, Synthetic
Structure-Activity Relationship
Trifluoroacetic Acid
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Summary:A new method for attaching aldehydes to solid supports has been developed employing a 2,2-bis(hydroxymethyl)propionic acid (DMPA ®) functionalized resin. High loading levels are obtained for both aryl and alkyl aldehydes protected as their respective acetals. Treatment of the derivatized resin with 95% TFA then cleanly affords the recovered aldehyde in high yield. A new method for attaching aldehydes to solid supports has been developed using a DMPA ® functionalized resin.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(98)00434-X