Issue 3, 2011

Nitrogen-directed ketone hydroacylation: Enantioselective synthesis of benzoxazecinones

Abstract

We report a nitrogen-directed ketone hydroacylation to furnish 8-membered N-containing lactones (benzoxazecinones) in high yields and high enantiomeric excesses. In a model study, a comparison was made between nitrogen, oxygen and sulfur directing groups and it was found that nitrogen promoted faster hydroacylation. Moreover, the amine directing group completely suppressed competitive decarbonylation. This catalytic transformation generates a relatively unexplored class of nitrogen heterocycles, namely benzoxazepinones and benzoxazecinones.

Graphical abstract: Nitrogen-directed ketone hydroacylation: Enantioselective synthesis of benzoxazecinones

Supplementary files

Article information

Article type
Edge Article
Submitted
05 Sep 2010
Accepted
25 Oct 2010
First published
30 Nov 2010

Chem. Sci., 2011,2, 407-410

Nitrogen-directed ketone hydroacylation: Enantioselective synthesis of benzoxazecinones

H. A. Khan, K. G. M. Kou and V. M. Dong, Chem. Sci., 2011, 2, 407 DOI: 10.1039/C0SC00469C

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