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Organocatalytic decarboxylative aldol reaction of β-ketoacids with α-ketophosphonates en route to the enantioselective synthesis of tertiary α-hydroxyphosphonates

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Abstract

The first example of an asymmetric organocatalyzed decarboxylative aldol reaction of β-ketoacids (aroylacetic acids) with α-ketophosphonates that produces a quaternary chiral centre has been developed. A quinidine based bifunctional urea derivative was identified as the preferred catalyst affording γ-aroyl tertiary α-hydroxyphosphonates in good yield and enantioselectivity. The 31P NMR spectroscopic study was performed to shed light on the reaction mechanism.

Graphical abstract: Organocatalytic decarboxylative aldol reaction of β-ketoacids with α-ketophosphonates en route to the enantioselective synthesis of tertiary α-hydroxyphosphonates

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Publication details

The article was received on 30 Mar 2017, accepted on 12 Apr 2017 and first published on 12 Apr 2017


Article type: Communication
DOI: 10.1039/C7OB00796E
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Organocatalytic decarboxylative aldol reaction of β-ketoacids with α-ketophosphonates en route to the enantioselective synthesis of tertiary α-hydroxyphosphonates

    G. B. Vamisetti, R. Chowdhury and S. K. Ghosh, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00796E

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