Issue 11, 2017

Exploiting intramolecular hydrogen bonding for the highly (Z)-selective & metal free synthesis of amide substituted β-aminoenones

Abstract

Herein, we report the metal free and intramolecular hydrogen bonding (IMHB) directed (Z)-selective synthesis of amide substituted β-aminoenones. Systematically, we confirm the role of dual IMHB (C[double bond, length as m-dash]O⋯H–N) on the Z-direction using single-crystal X-ray analysis and 1D and 2D NMR studies. High stereoselectivity, atom efficiency, excellent yields and high purity are achieved by mere filtration. We avoid column purification and the formed by-product in the process is environmentally friendly.

Graphical abstract: Exploiting intramolecular hydrogen bonding for the highly (Z)-selective & metal free synthesis of amide substituted β-aminoenones

Supplementary files

Article information

Article type
Communication
Submitted
24 Mar 2017
Accepted
04 May 2017
First published
05 May 2017

Green Chem., 2017,19, 2541-2545

Exploiting intramolecular hydrogen bonding for the highly (Z)-selective & metal free synthesis of amide substituted β-aminoenones

P. Subramaniam, C. Ramasubbu and S. Athiramu, Green Chem., 2017, 19, 2541 DOI: 10.1039/C7GC00909G

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