Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 10, Pages 1729-1734Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000835
Keywords
aldehydes; hydroxyphosphonates; ketophosphonates; organocatalysis; primary amines
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Funding
- NIH-NIGMS [SC1GM082718]
- Welch Foundation [AX-1593]
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The cross-aldol reaction between enolizable aldehydes and alpha-ketophosphonates was achieved for the first time by using 9-amino-9-deoxy-epi-quinine as the catalyst. beta-Formyl-alpha-hydroxyphosphonates were obtained in high to excellent enantioselectivities. The reaction works especially well with acetaldehyde, which is a tough substrate for organocatalyzed cross-aldol reactions. The products were demonstrated to have anticancer activities.
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