Issue 24, 2012

Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones

Abstract

N-Aryl 4-methylene-2-oxazolidinones, prepared via the corresponding O-propargyl carbamates, underwent nitrile oxide cycloaddition with benzonitrile oxide to give 5-spiro isoxazoline adducts with complete regioselectivity. Steric hindrance by atropisomerism around the N-aryl bond induced facial selectivity in these cycloadditions.

Graphical abstract: Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones

Supplementary files

Article information

Article type
Paper
Submitted
06 Feb 2012
Accepted
17 Apr 2012
First published
18 Apr 2012

Org. Biomol. Chem., 2012,10, 4759-4766

Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones

S. L. Harding and G. P. Savage, Org. Biomol. Chem., 2012, 10, 4759 DOI: 10.1039/C2OB25271F

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