Issue 29, 2012

Intramolecular cycloaddition of azomethine ylides, from imines of O-acylsalicylic aldehyde and ethyl diazoacetate, to estercarbonyl – experimental and DFT computational study

Abstract

Intramolecular 1,3-dipolar cycloaddition of alkoxycarbonyl-substituted azomethine ylides to ester carbonyl was realized for the first time in the reaction of imines of O-acylsalicylic aldehyde with ethyl diazoacetate in the presence of Cu(tfacac)2. The stereoselectivity of the cycloaddition is explained using DFT calculations.

Graphical abstract: Intramolecular cycloaddition of azomethine ylides, from imines of O-acylsalicylic aldehyde and ethyl diazoacetate, to ester carbonyl – experimental and DFT computational study

Supplementary files

Article information

Article type
Paper
Submitted
05 Apr 2012
Accepted
01 Jun 2012
First published
13 Jun 2012

Org. Biomol. Chem., 2012,10, 5582-5591

Intramolecular cycloaddition of azomethine ylides, from imines of O-acylsalicylic aldehyde and ethyl diazoacetate, to ester carbonyl – experimental and DFT computational study

A. P. Kadina, A. F. Khlebnikov, M. S. Novikov, P. J. Pérez and D. S. Yufit, Org. Biomol. Chem., 2012, 10, 5582 DOI: 10.1039/C2OB25676B

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