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Organocatalytic High Enantioselective Synthesis of ?-Formyl-?-hydroxyphosphonates.

ABSTRACT: The cross aldol reaction between enolizable aldehydes and ?-ketophosphonates was achieved for the first time by using 9-amino-9-deoxy-epi-quinine as the catalyst. ?-Formyl-?-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.

SUBMITTER: Perera S 

PROVIDER: S-EPMC3170695 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Organocatalytic High Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates.

Perera Sandun S   Naganaboina Vijaya Kumar VK   Wang Long L   Zhang Bin B   Guo Qunsheng Q   Rout Laxmidhar L   Zhao Cong-Gui CG  

Advanced synthesis & catalysis 20110601 10

The cross aldol reaction between enolizable aldehydes and α-ketophosphonates was achieved for the first time by using 9-amino-9-deoxy-epi-quinine as the catalyst. β-Formyl-α-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. ...[more]

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