Issue 18, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
30 Mar 2017
Accepted
12 Apr 2017
First published
12 Apr 2017

Org. Biomol. Chem., 2017,15, 3869-3873

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, 15, 3869 DOI: 10.1039/C7OB00796E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements