Issue 21, 2012

Solvent free l-proline-catalysed domino Knoevenagel/6π-electrocyclization for the synthesis of highly functionalised 2H-pyrans

Abstract

An environmentally benign synthesis of 2H-pyrans has been achieved in high yield using β-oxosulfones and 3,3-dialkylsubstituted α,β-unsaturated aldehydes. The key reaction is a solvent free L-proline catalysed domino Knoevenagel/6π-electrocyclization. As 3,3-dialkylsubstituted α,β-unsaturated aldehydes are a very common feature in many natural products, the transformation into highly functionalised 2H-pyrans makes this procedure a green and excellent method for a diversity oriented synthesis of biologically active compounds.

Graphical abstract: Solvent free l-proline-catalysed domino Knoevenagel/6π-electrocyclization for the synthesis of highly functionalised 2H-pyrans

Supplementary files

Article information

Article type
Paper
Submitted
28 Jun 2012
Accepted
03 Jul 2012
First published
04 Jul 2012

RSC Adv., 2012,2, 8041-8049

Solvent free L-proline-catalysed domino Knoevenagel/6π-electrocyclization for the synthesis of highly functionalised 2H-pyrans

J. Peña, R. F. Moro, P. Basabe, I. S. Marcos and D. Díez, RSC Adv., 2012, 2, 8041 DOI: 10.1039/C2RA21306K

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